EP3763352A1 - 2-(2,4,5-trimethylcyclohex-2-en-1-yl)acetaldehyd und derivate davon und deren verwendung als aromachemikalien - Google Patents

2-(2,4,5-trimethylcyclohex-2-en-1-yl)acetaldehyd und derivate davon und deren verwendung als aromachemikalien Download PDF

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EP3763352A1
EP3763352A1 EP19185187.2A EP19185187A EP3763352A1 EP 3763352 A1 EP3763352 A1 EP 3763352A1 EP 19185187 A EP19185187 A EP 19185187A EP 3763352 A1 EP3763352 A1 EP 3763352A1
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Prior art keywords
fragrance composition
mixture
iii
compound
compounds
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EP19185187.2A
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English (en)
French (fr)
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Melanie WEINGARTEN
Wolfgang Siegel
Silke Weyland
Ralf Pelzer
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BASF SE
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BASF SE
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Priority to EP19185187.2A priority Critical patent/EP3763352A1/de
Priority to MX2022000408A priority patent/MX2022000408A/es
Priority to CN202080049411.3A priority patent/CN114080380B/zh
Priority to US17/625,167 priority patent/US12319647B2/en
Priority to BR112021024094A priority patent/BR112021024094A2/pt
Priority to PCT/EP2020/069251 priority patent/WO2021005109A1/en
Priority to JP2022500654A priority patent/JP7574272B2/ja
Priority to EP20740557.2A priority patent/EP3997057A1/de
Publication of EP3763352A1 publication Critical patent/EP3763352A1/de
Withdrawn legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
    • C07C43/14—Unsaturated ethers
    • C07C43/162—Unsaturated ethers containing rings other than six-membered aromatic rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q13/00—Formulations or additives for perfume preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/10—Washing or bathing preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/02—Preparations for cleaning the hair
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
    • C07C33/05—Alcohols containing rings other than six-membered aromatic rings
    • C07C33/14—Alcohols containing rings other than six-membered aromatic rings containing six-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/18—Ethers having an ether-oxygen atom bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C07C43/188—Unsaturated ethers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/30—Compounds having groups
    • C07C43/303—Compounds having groups having acetal carbon atoms bound to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
    • C07C69/12—Acetic acid esters
    • C07C69/14—Acetic acid esters of monohydroxylic compounds
    • C07C69/145—Acetic acid esters of monohydroxylic compounds of unsaturated alcohols
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B9/00—Essential oils; Perfumes
    • C11B9/0026—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring
    • C11B9/0034—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring the ring containing six carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/2068—Ethers
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/2072—Aldehydes-ketones
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/2093—Esters; Carbonates
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/50—Perfumes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated

Definitions

  • the present invention relates to 2-(2,4,5-trimethylcyclohex-2-en-1-yl)acetaldehyde and derivatives thereof, to a process for preparing said compounds, to the use of 2-(2,4,5-trimethylcyclohex-2-en-1-yl)acetaldehyde or a specific derivative thereof or of mixtures of said compounds or of a stereoisomer thereof or of a mixture of two or more stereoisomers thereof as aroma chemicals; to the use of 2-(2,4,5-trimethylcyclohex-2-en-1-yl)acetaldehyde or a specific derivative thereof for modifying the scent character of a fragranced composition; to compositions containing 2-(2,4,5-trimethylcyclohex-2-en-1-yl)acetaldehyde or a specific derivative thereof or a mixture of said compounds or a stereoisomer thereof or a mixture of two or more stereoisomers thereof; and to a method of preparing a fragranced composition or for modifying the scent character of a fragranced composition
  • Aroma chemicals, especially fragrances, are of great interest especially in the field of cosmetics and cleaning and laundry compositions. Fragrances of natural origin are mostly expensive, often limited in their available amount and, on account of fluctuations in environmental conditions, are also subject to variations in their content, purity etc. To circumvent these undesirable factors, it is therefore of great interest to create synthetic substances which have organoleptic properties that resemble more expensive natural fragrances or which have novel and interesting organoleptic profiles.
  • aroma chemicals fragments and flavorings
  • organoleptic properties i.e. the compounds should have advantageous odiferous (olfactory) or gustatory properties.
  • aroma chemicals should also have additional positive secondary properties, such as e.g. an efficient preparation method, the possibility of providing better sensory profiles as a result of synergistic effects with other fragrances, a higher stability under certain application conditions, a higher extendability, a better substantivity, etc.
  • the invention relates to a compound of the general formula (I) wherein
  • Another aspect of the present invention relates to a compound of the general formula (II) wherein
  • Another aspect of the invention relates to a compound of the general formula (III) a stereoisomer thereof or a mixture of stereoisomers thereof.
  • Yet another aspect of the invention relates to a process for preparing a compound of the general formula (I), or a mixture of two or more compounds of the general formula (I) or a stereoisomer thereof or a mixture of two or more stereoisomers thereof, according to any of claims 1 to 4, which process comprises:
  • Another aspect of the invention relates to the use of a compound of formulae (I), (II), (III) or (IV) or of a mixture of two or more compounds of the general formulae (I), (II), (III) and (IV), or of a stereoisomer thereof or of a mixture of two or more stereoisomers thereof as an aroma chemical.
  • Another aspect of the invention relates to the use of a compound of formulae (I), (II), (III) or (IV) or of a mixture of two or more compounds of the general formulae (I), (II), (III) and (IV), or of a stereoisomer thereof or of a mixture of two or more stereoisomers thereof for modifying the scent character of a fragranced composition
  • compositions comprising a compound of formulae (I), (II), (III) or (IV) or a mixture of two or more compounds of the general formulae (I), (II), (III) and (IV), or of a stereoisomer thereof or of a mixture of two or more stereoisomers thereof, and at least one further component selected from the group consisting of aroma chemicals, non-aroma chemical carriers, anti-oxidants and deodorant-active agents.
  • the invention also relates to a method for preparing a fragranced composition or for modifying the scent character of a fragranced composition comprising incorporating a compound of formulae (I), (II), (III) or (IV) or a mixture of two or more compounds of the general formulae (I), (II), (III) and (IV), or of a stereoisomer thereof or of a mixture of two or more stereoisomers thereof into said composition.
  • the compounds of formulae (I), (II), (III) and (IV) as well as mixtures of two or more compounds of the general formulae (I), (II), (III) and (IV), their stereoisomers and the mixtures of their stereoisomers have particularly good, virtually universal solvent properties for and in aroma chemicals and other customary ingredients in compositions such as, in particular, fragrance compositions.
  • the compounds of formulae (I), (II), (III) and (IV) as well as mixtures of two or more compounds of the general formulae (I), (II), (III) and (IV), their stereoisomers and the mixtures of their stereoisomers are favorably combinable with aroma chemicals, allowing, in particular, the creation of aroma compositions, in particular fragrance compositions, having novel advantageous sensory profiles.
  • the compounds of formulae (I), (II), (III) and (IV) as well as mixtures of two or more compounds of the general formulae (I), (II), (III) and (IV), their stereoisomers and the mixtures of their stereoisomers can be produced in good yields and purities by a simple and economic synthesis, starting from readily available malodorous 2,5,6-trimethylcyclohex-2-en-1-one.
  • the compounds of formulae (I), (II), (III) and (IV) as well as mixtures of two or more compounds of the general formulae (I), (II), (III) and (IV), their stereoisomers and the mixtures of their stereoisomers can be produced in large scales in a simple and cost-efficient manner.
  • C 2 -C 4 -alkyl refers to a linear or branched saturated hydrocarbon radical having 2 to 4 carbon atoms.
  • C 2 -C 4 -Alkyl is ethyl, propyl, isopropyl, n-butyl, 1-methylpropyl (sec-butyl), 2-methylpropyl (-butyl) or 1,1-dimethylethyl (tert-butyl).
  • C 2 -C 4 -alkylene refers to a linear or branched divalent alkanediyl radical having 2 to 4 carbon atoms.
  • C 2 -C 2 -alkylene are for example 1,2-ethylene, 1,1-ethylene, 1,3-propylene, 1,2-propylene, 1,4-butylene, 1,3-butylene, 1,2-butylene or 2,3-butylene.
  • the compounds of the formula (I) can be present in the form of the pure stereoisomers or in the form of stereoisomer mixtures.
  • the present invention relates to the single pure stereoisomers of the compounds of the general formula (I) as well as to mixtures of two or more stereoisomers thereof.
  • stereoisomers encompasses optical isomers, such as enantiomers or diastereomers, the latter existing due to more than one stereogenic center in the molecule.
  • the compounds of the formula (I) have 3 stereogenic centers, i.e. the carbon-atoms in the 1-, 4- and 5-position of the cyclohexene ring.
  • the invention provides both the pure enantiomers or diastereomers of the compounds (I) and mixtures thereof and the use according to the invention of the pure enantiomers or pure diastereomers of the compounds (I) or mixtures thereof.
  • the term "pure enantiomer" has to be understood as a non-racemic mixture of a specific compound, where the desired enantiomer is present in an enantiomeric excess of > 90%ee.
  • the term "pure diastereomer” has to be understood as a mixture of the diastereomers of a specific compound, where the desired diastereomer is present in an amount of > 90%, based on the total amount of diastereomers of said compound.
  • compound (I) or “compound of formula (I)" when not defined as a specific stereoisomer or a specific mixture of stereoisomers, refers to the form of the compound as it is obtained in a non-stereoselective method used for its production. The term is however also used if it is not necessary or not possible to specify in more detail the stereochemistry of the compound (I).
  • X represents a group X 1 , X 2 or X 3 , more preferably a group X 1 or X 2 .
  • X represents a group X 1 .
  • R 1 is hydrogen or methyl.
  • R 2 is methyl or ethyl.
  • R 3 is methyl, ethyl or phenyl, in particular methyl or ethyl.
  • a preferred embodiment of the present invention relates to compounds of the general formula (I) wherein
  • Examples of preferred compounds I are 2-(2,4,5-trimethylcyclohex-2-en-1-yl)acetaldehyde, 2-(2,4,5-trimethylcyclohex-2-en-1-yl)ethanol, 6-(2-methoxyethyl)-1 ,3,4-trimethyl-cyclohexene, 6-(2-ethoxyethyl)-1,3,4-trimethyl-cyclohexene, 2-(2,4,5-trimethylcyclohex-2-en-1-yl)ethyl acetate, 2-(2,4,5-trimethylcyclohex-2-en-1-yl)ethyl propanoate, methyl 2-(2,4,5-trimethylcyclohex-2-en-1-yl)ethyl carbonate, ethyl 2-(2,4,5-trimethylcyclohex-2-en-1-yl)ethyl carbonate, a mixture thereof, a stereoisomer thereof or a mixture of stereoisomers thereof.
  • a more preferred embodiment of the present invention relates to compounds of the general formula (I) wherein
  • the compound (I) or the mixtures of compounds (I), as described herein may predominantly be present in the form of a stereoisomer or mixtures of two or more stereoisomers of the general formula (I-R) wherein the radical X, as well as the radicals R 1 , R 2 and R 3 , if present, have one of the meanings given above.
  • the compounds (I) or the mixtures of compounds (I), as described herein may predominantly be present in the form of a stereoisomer or mixtures of two or more stereoisomers of the general formula (I-S) wherein the radical X, as well as the radicals R 1 , R 2 and R 3 , if present, have one of the meanings given above.
  • stereoisomers of the general formula (I-R) or (I-S) means, that at least 70% by weight, preferably at least 80% by weight, more preferably at least 90% by weight, even more preferably at least 95% by weight, in particular at least 98% by weight of the compounds (I), are present in the form of its stereoisomers (I-R) or (I-S).
  • a particular embodiment of the present invention relates to a compound of the formula (I.a) a stereoisomer thereof or a mixture of stereoisomers thereof.
  • the compound I.a is predominantly present in the form of a stereoisomer or mixtures of two or more stereoisomers of the general formula (I.a-R)
  • Specific compounds of the formulae (I.a-R) are 2-[(1R,4R,5R)-2,4,5-trimethylcyclohex-2-en-1-yl]acetaldehyde, 2-[(1R,4R,5S)-2,4,5-trimethylcyclohex-2-en-1-yl]acetaldehyde, 2-[(1R,4S,5R)-2,4,5-trimethylcyclohex-2-en-1-yl]acetaldehyde, 2-[(1R,4S,5S)-2,4,5-trimethylcyclohex-2-en-1-yl]acetaldehyde, or a mixture thereof.
  • the compound I.a is predominantly present in the form of a stereoisomer or mixtures of two or more stereoisomers of the general formula (I.a-S)
  • Specific compounds of the formulae (I.a-S) are 2-[(1S,4R,5R)-2,4,5-trimethylcyclohex-2-en-1-yl]acetaldehyde, 2-[(1S,4R,5S)-2,4,5-trimethylcyclohex-2-en-1-yl]acetaldehyde, 2-[(1S,4S,5R)-2,4,5-trimethylcyclohex-2-en-1-yl]acetaldehyde, 2-[(1S,4S,5S)-2,4,5-trimethylcyclohex-2-en-1-yl]acetaldehyde, or a mixture thereof.
  • stereoisomers of the general formula (I.a-R) or (I.a-S) means, that at least 70% by weight, preferably at least 80% by weight, more preferably at least 90% by weight, even more preferably at least 95% by weight, in particular at least 98% by weight of the compounds (I.a), are present in the form of its stereoisomers (I.a-R) or (I.s-S).
  • the compounds of the general formula (II) can be present in the form of the pure stereoisomers or in the form of stereoisomer mixtures, depending on the isomeric purity of the starting materials and method of manufacturing, e.g. the applied reaction conditions and applied workup/purification procedures.
  • the present invention relates to the single pure stereoisomers of the compounds of the general formula (II) as well as to mixtures of two or more stereoisomers thereof.
  • the compounds of the formula (II) have at least 3 stereogenic centers, i.e. the carbon-atoms in the 4- and 5-position of the cyclohexene ring carrying the methyl groups as well as the carbon atom at the 6-position of the cyclohexene ring, which carries the acetal group.
  • the invention provides both the pure enantiomers or diastereomers of the compounds (II) and mixtures thereof and the use according to the invention of the pure enantiomers or pure diastereomers of the compounds (II) or mixtures thereof.
  • the compound (II) or the mixtures of compounds (II), as described herein may predominantly be present in the form of a stereoisomer or mixtures of two or more stereoisomers of the general formula (II-R) or in the form of a stereoisomer or mixtures of two or more stereoisomers of the general formula (II-S) wherein R 4 has one of the meanings given above or below.
  • stereoisomers of the general formula (II-R) or (II-S) means, that at least 90% by weight, preferably at least 95% by weight, more preferably at least 98% by weight, in particular at least 99% by weight of the compounds (II), are present either in the form of its stereoisomers (II-R) or in the form of its stereoisomers (II-S).
  • R 4 is C 2 -C 4 -alkyl, or 2-vinyloxyethyl.
  • R 4 is C 2 -C 4 -alkyl, even more preferably ethyl, propyl or isobutyl, in particular ethyl or isobutyl, especially ethyl.
  • Preferred compounds of the general formula (II) are for example (6R)-6-(1-ethoxyethoxy)-1,4,5-trimethyl-cyclohexene, (6S)-6-(1-ethoxyethoxy)-1,4,5-trimethyl-cyclohexene, (6R)-6-(1-propoxyethoxy)-1,4,5-trimethyl-cyclohexene, (6S)-6-(1-propoxyethoxy)-1,4,5-trimethyl-cyclohexene, (6R)-6-(1-isobutoxyethoxy)-1,4,5-trimethyl-cyclohexene, (6S)-6-(1-isobutoxyethoxy)-1,4,5-trimethyl-cyclohexene, (6R)-1,4,5-trimethyl-6-[1-(1-methyl-2-vinyloxy-ethoxy)ethoxy]cyclohexene, (6S)-1,4,5-trimethyl-6-[1-(1-methyl-2-vinyloxy-e
  • the compounds of the general formula (III) can be present in the form of the pure stereoisomers or in the form of stereoisomer mixtures, depending on the isomeric purity of the starting materials and method of manufacturing, e.g. the applied reaction conditions and applied workup/purification procedures.
  • the present invention relates to the single pure stereoisomers of the compounds of the general formula (III) as well as to mixtures of two or more stereoisomers thereof.
  • the compounds of the formula (III) have at least 3 stereogenic centers, i.e. the carbon-atoms in the 4- and 5-position of the cyclohexene ring carrying the methyl groups as well as the carbon atom at the 6-position of the cyclohexene ring, which carries the vinyloxy group.
  • the invention provides both the pure enantiomers or diastereomers of the compounds (III) and mixtures thereof and the use according to the invention of the pure enantiomers or pure diastereomers of the compounds (III) or mixtures thereof.
  • the compounds (III), as described herein may predominantly be present in the form of a stereoisomer or mixtures of two or more stereoisomers of the general formula (III-R) or in the form of a stereoisomer or mixtures of two or more stereoisomers of the general formula (III-S)
  • stereoisomers of the general formula (III-R) or (III-S) means, that at least 90% by weight, preferably at least 95% by weight, more preferably at least 98% by weight, in particular at least 99% by weight of the compounds (III), are present either in the form of its stereoisomers (III-R) or in the form of its stereoisomers (III-S).
  • the compound of formula (III) is a compound of the general formulae (III-R) or (III-S) a stereoisomer thereof or a mixture of stereoisomers thereof.
  • Preferred compounds of the general formula (III-R) are (4R,5R,6R)-1,4,5-trimethyl-6-vinyloxy-cyclohexene, (4S,5R,6R)-1,4,5-trimethyl-6-vinyloxy-cyclohexene, (4R,5S,6R)-1,4,5-trimethyl-6-vinyloxy-cyclohexene, (4S,5S,6R)-1,4,5-trimethyl-6-vinyloxy-cyclohexene, and mixtures thereof.
  • Preferred compounds of the general formula (III-S) are (4R,5R,6S)-1,4,5-trimethyl-6-vinyloxy-cyclohexene, (4S,5R,6S)-1,4,5-trimethyl-6-vinyloxy-cyclohexene, (4R,5S,6S)-1,4,5-trimethyl-6-vinyloxy-cyclohexene, and (4S,5S,6S)-1,4,5-trimethyl-6-vinyloxy-cyclohexene, and mixtures thereof.
  • the compounds of the general formulae (II) and (III) are intermediates in the production process of compounds (I) as described below.
  • the intermediates (III) are produced from the acetal precursors (II) via elimination of the alcohol R 4 -OH. Since this elimination reaction of the acetals (II) may also occur simultaneously to the formation of the acetals (II), the intermediates (II) may comprise significant amounts of compounds (III).
  • the compounds (III) may also spontaneously undergo an in situ Claisen rearrangement to the corresponding aldehyde compounds, i.e. to the compounds of the general formula (I), wherein X represents the group X 1 .
  • the present invention relates to a mixture of compounds comprising two or three compounds selected from:
  • the total amount of the compound (II), if present, and the compounds (III) and (I), wherein X represents the group X 1 , in the aforesaid compound mixtures is typically 70% by weight, preferably at least 80% by weight, more preferably at least 90% by weight, in particular at least 95% by weight, based on the total weight of the mixture.
  • the aforesaid mixtures do not comprise significant or even no detectable amounts of compounds of the general formula (I), wherein X represents the group X 1 .
  • the total amount of the compounds (II) and (III) in the aforesaid compound mixtures is typically 70% by weight, preferably at least 80% by weight, more preferably at least 90% by weight, in particular at least 95% by weight, based on the total weight of the mixture.
  • the total amount of the compounds (II) and the compounds (I), wherein X represents the group X 1 , in the aforesaid compound mixtures is typically 70% by weight, preferably at least 80% by weight, more preferably at least 90% by weight, in particular at least 95% by weight, based on the total weight of the mixture.
  • the compounds (I) are produced from 2,5,6-trimethylcyclohex-2-en-1-one and 2,5,6-trimethylcyclohex-2-en-1-ol (IV), respectively.
  • 2,5,6-trimethylcyclohex-2-en-1-one is a malodorous compound, which cannot be used as an aroma chemical.
  • the compounds (I) as well as the compounds (II), (III) and (IV), as defined herein, should therefore contain as little as possible, preferably no residual amounts of the starting material 2,5,6-trimethylcyclohex-2-en-1-one.
  • the compounds (I) as well as the compounds (II) and (III), as defined herein can efficiently be obtained from 2,5,6-trimethylcyclohex-2-en-1-one by the process described below, without comprising detectable amounts of 2,5,6-trimethylcyclohex-2-en-1-one.
  • the compounds (IV) can efficiently be obtained from 2,5,6-trimethylcyclohex-2-en-1-one by the process described below, without comprising detectable amounts or at least without comprising noticeable amounts of 2,5,6-trimethylcyclohex-2-en-1-one.
  • a specific embodiment of the present invention relates to compounds or mixture of compounds of the general formulae (I), (II), (III) or (IV), as defined herein, comprising at most 1% by weight, preferably at most 0.5% by weight, in particular at most 0.1% by weight of 2,5,6-trimethylcyclohex-2-en-1-one, based on the total weight of the compounds or mixture of compounds.
  • An even more specific embodiment of the present invention relates to compounds or mixture of compounds of the general formula (I), (II) or (III), as defined herein, comprising at most 1 % by weight, preferably at most 0.5% by weight, in particular at most 0.1% by weight of 2,5,6-trimethylcyclohex-2-en-1-one and at most 5% by weight, preferably at most 3% by weight, more preferably at most 2% by weight, in particular at most 1% by weight of 2,5,6-trimethylcyclohex-2-en-1-ol, based on the total weight of the compounds or mixture of compounds.
  • a further specific embodiment of the present invention relates to compounds of the general formula (IV), as defined herein, comprising at most 1% by weight, preferably at most 0.5% by weight, in particular at most 0.1% by weight, of 2,5,6-trimethylcyclohex-2-en-1-one, based on the total weight of the compounds (IV).
  • An even more specific embodiment of the present invention relates to compounds or mixture of compounds of the general formula (I), (II), (III) or (IV), as defined herein, comprising no detectable amounts of 2,5,6-trimethylcyclohex-2-en-1-one.
  • a special embodiment of the present invention relates to compounds or mixture of compounds of the general formula (I), (II) or (III), as defined herein, comprising no detectable amounts of 2,5,6-trimethylcyclohex-2-en-1-one and 2,5,6-trimethylcyclohex-2-en-1-ol, respectively.
  • the present invention further relates to a process for preparing a compound of the general formula (I), or a mixture of two or more compounds of the general formula (I) or a stereoisomer thereof or a mixture of two or more stereoisomers thereof, according to any of claims 1 to 4, which process comprises:
  • step (i) of the process of the present invention 2,5,6-trimethylcyclohex-2-en-1-ol (IV) is provided.
  • 2,5,6-trimethylcyclohex-2-en-1-ol can be prepared by using standard methods of organic chemistry that are known to the skilled person.
  • the 2,5,6-trimethylcyclohex-2-en-1-ol (IV) provided in step (i) is obtained by subjecting 2,5,6-trimethylcyclohex-2-en-1-one (VI) to a selective reduction reaction of the carbonyl group to a hydroxyl group.
  • any method known to the skilled person for the selective reduction of the carbonyl group of ⁇ , ⁇ -unsaturated ketones to afford the corresponding ⁇ , ⁇ -unsaturated alcohols can be applied for the selective reduction of 2,5,6-trimethylcyclohex-2-en-1-one (VI) to 2,5,6-trimethylcyclohex-2-en-1-ol (IV).
  • 2,5,6-trimethylcyclohex-2-en-1-one can be selectively reduced using heterogeneous metal catalysts, such as chromium-promoted Raney nickel in methanol, cobalt oxide or Raney cobalt, in the presence of a strong mineral base, or by using MgO or Magnesium-aluminum mixed oxide (MgO/Al 2 O 3 ) in the presence of 2-propanol (Meerwein-Ponndorf-Verley type reduction), as e.g. described in the " Handbook of heterogeneous catalytic hydrogenation for organic synthesis" by S. Nishimura, chapter 5.3.5: "unsaturated ketones", pp. 198 - 200 .
  • heterogeneous metal catalysts such as chromium-promoted Raney nickel in methanol, cobalt oxide or Raney cobalt
  • the chemoselective reduction of 2,5,6-trimethylcyclohex-2-en-1-one (VI) to 2,5,6-trimethylcyclohex-2-en-1-ol (IV) may also be performed in the presence of metal hydrides, such as Zn(BH 4 ) 2 , NaBH 4 / CeCl 3 , LiAlH 4 , Li n -BuBH 3 or 9-bora-bicyclo[3.3.1]nonane (9-BBN), as for example described by Cha et al., Bull. Korean Chem. Soc. (2007), 28(12), pp. 2162-2190 , Cha et al., Bull. Korean Chem. Soc.
  • metal hydrides such as Zn(BH 4 ) 2 , NaBH 4 / CeCl 3 , LiAlH 4 , Li n -BuBH 3 or 9-bora-bicyclo[3.3.1]nonane (9-BBN
  • 2,5,6-trimethylcyclohex-2-en-1-one (VI) can be selectively reduced to 2,5,6-trimethylcyclohex-2-en-1-ol (IV) in the presence of catalytic amounts of phosphine stabilized Cu-H complexes and stoichiometric amounts of (alkyl/aryl/alkoxy)-silanes, as for example described in " Topics in Organometallic Chemistry", 2016, 58, pp. 207-220 , and the references cited therein.
  • the enantioselective reduction of 2,5,6-trimethylcyclohex-2-en-1-one (VI) to either (1R)- or (1S)-2,5,6-trimethylcyclohex-2-en-1-ol (IV) can by way of example be performed by using chiral hydride reagents, e.g. by using lithium aluminium hydride modified with chiral alkoxide ligands such as BINOL, as for example described by Chan et al., J. Org. Chem. (1988), 53, 5584-5586 , or by using chiral alkylborohydrides, as for example described by Ramachandran et al., Tetrahedron: Asymmetry (1990), 1, 433 .
  • chiral hydride reagents e.g. by using lithium aluminium hydride modified with chiral alkoxide ligands such as BINOL, as for example described by Chan et al., J. Org. Chem. (1988
  • chiral transition metal catalysts enantioselective Meerwein-Ponndorf-Verley type reduction.
  • Suitable chiral transition metal catalysts are for example Ru, Rh, Ir or Sm complexes with chiral diamine ligands, chiral aminoalcohol ligands, chiral bisphosphine ligands or chiral bis(oxazoline) ligands.
  • chiral phosphine ligands / Cu-H complexes may be used as chiral catalysts, as for example described by Moser et al., J. Am. Chem. Soc., 2010, 132(23), pp. 7852-7853 .
  • the enantioselective reduction of 2,5,6-trimethylcyclohex-2-en-1-one (VI) to either (1R)- or (1S)-2,5,6-trimethylcyclohex-2-en-1-ol (IV) may also be performed enzymatically by using suitable alcoholdehydrogenases or by using microorganisms, such as specifically modified baker's yeast.
  • the selective reduction reaction of 2,5,6-trimethylcyclohex-2-en-1-one (VI) to 2,5,6-trimethylcyclohex-2-en-1-ol (IV) is performed in the presence of metal hydrides, as defined above.
  • the metal hydride is selected from NaBH 4 , NaBH 4 / CeCl 3 , Zn(BH 4 ) 2 , LiAlH 4 , Li n -BuBH 3 and 9-BBN.
  • the selective reduction reaction is typically carried out in an inert solvent, i.e. a solvent that does not react with the starting materials, intermediates and reagents applied in the reduction reaction or with the obtained products.
  • Suitable solvents are for example alcohols, such as methanol, ethanol, propanol and isopropanol; aromatic and substituted aromatic hydrocarbons, such as benzene, chlorobenzene, dichlorobenzenes, toluene, xylene; and aliphatic hydrocarbons, such as pentane, hexanes, cyclohexane, heptanes, octanes, nonanes, decanes, ligroin and petrol ether, halogenated aliphatic hydrocarbons, such as dichloromethane, trichloromethane and tetrachloromethane, ethers, such as diethyl ether, dibutyl ether, THF, 1,4-di
  • the metal hydride reagent is typically applied in stoichiometric amounts. However, depending on the reactivity and the number of hydride-ions (hydride equivalents) that is delivered by the hydride reagent as well as the type of solvent applied in the reduction reaction, the final amount of the added hydride reagent typically varies within a broad range.
  • the metal hydride reagent is added in several portions, e.g. in 2, 3, 4, 5, 10, 15 or 20 portions or continuously over a time period of from 5 minutes to 5 hours, preferably over a time period of 20 minutes to 3 hours to the reaction mixture comprising 2,5,6-trimethylcyclohex-2-en-1-one (VI).
  • 2,5,6-trimethylcyclohex-2-en-1-one (VI) may be added in several portions, e.g. in 2, 3, 4, 5, 10, 15 or 20 portions or continuously over a time period of from 5 minutes to 5 hours, preferably over a time period of 20 minutes to 3 hours to the reaction mixture comprising the total amount of the metal hydride reagent.
  • the selective reduction reaction of this preferred embodiment is typically performed at low reaction temperatures, i.e. at reaction temperatures in the range of from -20 to 20°C, preferably in the range of from -10 to 15°C, in particular in the range of from -5 to 10°C.
  • the selective reduction reaction of 2,5,6-trimethylcyclohex-2-en-1-one (VI) to 2,5,6-trimethylcyclohex-2-en-1-ol (IV) is performed under Meerwein-Ponndorf-Verley type conditions using organometallic reagents, preferably organo-boron and organo-aluminium reagents, in particular diisopinocampheylboron and diisobutylaluminum derivatives.
  • organometallic reagents preferably organo-boron and organo-aluminium reagents, in particular diisopinocampheylboron and diisobutylaluminum derivatives.
  • the selective reduction reaction is typically carried out in an inert solvent, i.e. a solvent that does not react with the starting materials, intermediates and reagents applied in the reduction reaction or with the obtained products.
  • Suitable solvents are for example aliphatic hydrocarbons, such as pentane, hexanes, cyclohexane, heptanes, octanes, nonanes, decanes, ligroin and petrol ether; halogenated aliphatic hydrocarbons, such as dichloromethane, trichloromethane and tetrachloromethane; ethers, such as diethyl ether, dibutyl ether, THF, 1,4-dioxane, 1,2-dimethoxyethane; as well as mixtures thereof.
  • the organometallic reagent is typically applied in stoichiometric amounts. However, depending on the reactivity and the nature of the organometallic reagent the amount of the organometallic reagent applied in the selective reduction reaction typically varies within a broad range. Typically, the organometallic reagent is added in amounts of from 0.5 to 5 equivalents, preferably in amounts of from 0.8 to 3 equivalents, per 1 equivalent of carbonyl compound.
  • reaction temperature for the selective reduction reaction of this preferred embodiment greatly varies depending on the reactivity of the applied organometallic reagent.
  • the reduction of carbonyl groups can only be effected at rather high reaction temperatures, e.g. at reaction temperatures in the range of from 80 to 150°C, whereas if diisopinocampheylhalo-boranes (Ipc 2 BX) are used as the organometallic reagent, the reduction of carbonyl groups can be performed at reaction temperatures as low as -25 to 0°C.
  • the reaction temperatures are typically in the range of from -15 to 45°C, preferably in the range of from -5 to 35°C.
  • 2,5,6-trimethylcyclohex-2-en-1-one (VI), which is used as the preferred starting material, can typically be purchased as a mixture of stereoisomers, i.e. a mixture of cis-2,5,6-trimethylcyclohex-2-en-1-one (5R,6R-2,5,6-trimethylcyclohex-2-en-1-one and 5S,6S-2,5,6-trimethylcyclohex-2-en-1-one, hereinafter referred to as cis-VI) and trans-2,5,6-trimethylcyclohex-2-en-1-one (5R,6S-2,5,6-trimethylcyclohex-2-en-1-one and 5S,6R-2,5,6-trimethylcyclohex-2-en-1-one, hereinafter referred to as trans-VI).
  • trans-VI trans-2,5,6-trimethylcyclohex-2-en-1-one
  • the ketone 2,5,6-trimethylcyclohex-2-en-1-one (VI) can be prepared by using standard methods of organic chemistry that are known to the skilled person.
  • step (VI) is applied in the reaction of step (i) either in the form of one of its pure stereoisomers or in the form of stereoisomer mixtures.
  • 2,5,6-trimethylcyclohex-2-en-1-one (VI) is applied in the form of stereoisomer mixtures.
  • step (i) 2,5,6-trimethylcyclohex-2-en-1-one (VI) is applied in the reaction of step (i) in the form of mixtures of all 4 stereoisomers, wherein the ratio of the trans-VI stereoisomers to the cis-VI stereoisomers is in the range of from 55:45 to 90:10, even more preferably in the range of from 60:40 to 80:20, in particular in the range of from 65:35 to 75:25.
  • 2,5,6-trimethylcyclohex-2-en-1-one (VI) may comprise lower amounts, e.g. at most 5% by weight, preferably at most 2% by weight, in particular at most 1.5% by weight of the corresponding saturated 2,3,6-trimethylcyclohexane-1-one isomers.
  • step (ii) of the process of the present invention the 2,5,6-trimethylcyclohex-2-en-1-ol (IV) provided in step (i) is reacted with a vinylether of the general formula (V) wherein
  • the catalyst applied in step (ii) is selected from Br ⁇ nsted acids and Lewis acids and mixtures thereof. More preferably, the catalyst applied in step (ii) is selected from weak to moderately strong Br ⁇ nsted acids and soft to moderately hard Lewis acids.
  • Br ⁇ nsted acids which have a pKa value in water in the range of from 6 to 0.5, preferable in the range of from 5.2 to 1, in particular in the range of from 4.9 to 1.5.
  • Br ⁇ nsted acids are for example phosphoric acid, phosphonic acids, such as methylphosphonic acid, ethylphosphonic acid, propylphosphonic acid or phenylphosphonic acid and carboxylic acids, such as oxalic acid, chloroacetic acid, citric acid, tartaric acid, formic acid, acetic acid and propionic acid.
  • Suitable Lewis acids that can be applied in step (ii) are for example Fe(III)acetylacetonate, Fe(III)Cl 3 , Yb(III)triflate, Bi(III)triflate, MgCl 2 , Fe(II)acetylacetonate, Fe(II)acetate, Fe(II)triflate, Fe(II)Cl 2 , Ni(II)acetylacetonate, Ni(II)acetate, Ni(II)triflate, Ni(II)Cl 2 , Co(II)acetylacetonate, Co(II)acetate, Co(II)triflate, Co(II)Cl 2 , Cu(II)acetylacetonate, Cu(II)acetate, Cu(II)triflate, Cu(II)Cl 2 , Hg(II)acetylacetonate, Hg(II)acetate, Hg(II)triflat
  • Pd(II)Cl 2 (MeCN) 2 Pt(II)acetylacetonate, Pt(II)acetate, Pt(II)triflate, Pt(II)Cl 2 , Cd(II)acetylacetonate, Cd(II)acetate, Cd(II)triflate, Cd(II)Cl 2 , Cu(I)acetate, Cu(I)triflate, Cu(I)Cl, Ag(I)acetate, Ag(I)triflate, Au(I)acetate, Au(I)triflate and Ag(I)Cl.
  • the catalyst applied in step (ii) is selected from phosphoric acid; phosphonic acids, such as methylphosphonic acid, ethylphosphonic acid, propylphosphonic acid and phenylphosphonic acid; carboxylic acids, such as formic acid, oxalic acid, chloroacetic acid, citric acid, tartaric acid, acetic acid and propionic acid; and soft to moderately hard Lewis acids, such as Fe(III)acetylacetonate, Yb(III)triflate, Bi(III)triflate, MgCl 2 , Fe(II)acetylacetonate, Fe(II)acetate, Fe(II)triflate, Ni(II)acetylacetonate, Ni(II)acetate, Ni(II)triflate, Co(II)acetylacetonate, Co(II)acetate, Co(II)triflate, Cu(II)acetylacetonate, Cu(II)ace
  • Pd(II)Cl 2 (MeCN) 2 Pt(II)acetylacetonate, Pt(II)acetate, Pt(II)triflate, Cd(II)acetylacetonate, Cd(II)acetate, Cd(II)triflate, Cu(I)acetate, Cu(I)triflate, Ag(I)acetate, Ag(I)triflate, Au(I)acetate and Au(I)triflate.
  • the catalyst applied in step (ii) is selected from phosphoric acid, phenylphosphonic acid, formic acid, acetic acid, propionic acid, Fe(III)acetylacetonate, Cu(II)acetate, Cu(I)acetate, Hg(II)acetate, Pd(II)acetate, Pd(II)triflate and Pd(II)Cl 2 , e.g. Pd(II)Cl 2 (MeCN) 2 .
  • the reaction in step (ii) proceeds via the formation of two intermediate compounds, i.e. compounds of the general formulae (II) and (III), as depicted in scheme 1.
  • the alcohol group of 2,5,6-trimethyl-cyclohex-2-en-1-ol first adds to the vinyl group of compounds (V) resulting in the formation of the acetal intermediates (II).
  • These acetal intermediates (II) further react to the vinyl ether intermediate (III) by eliminating the alcohol R 4 -OH.
  • the vinyl ether intermediate (III) in turn undergoes a Claisen rearrangement to form the corresponding aldehyde compounds, i.e. the compounds of the general formula (I), wherein the group X represents the aldehyde group X 1 .
  • the reaction in step (ii) of the present invention may stop at the acetal intermediate (II) and/or the vinylether intermediate (III) (two or three step reaction) or will directly provide the desired aldehyde compounds of formula (I), wherein X represents a group X 1 (one step reaction).
  • the 2,5,6-trimethylcyclohex-2-en-1-ol is first reacted with a vinylether of the general formula (V) to the first intermediate compound, i.e. the acetal of the general formula (II).
  • the acetal intermediates (II) can be isolated, i.e. subjected to a work-up and/or purification procedure, before they are further converted to the second intermediate compound, i.e. the vinylether intermediate (III), or to the final aldehyde compounds of formula (I), wherein X represents a group X 1 , through subsequent Claisen rearrangement.
  • the obtained acetal intermediates (II) can be directly applied to the further conversion reactions. If the acetal intermediates (II) are not directly converted to the final aldehyde compound (I) but first to the vinylether intermediates (III), these vinylethers (III) may also be isolated before they are subjected to the final Claisen rearrangement reaction. Alternatively, the vinylethers (III) can also be directly applied to the final Claisen rearrangement reaction, without prior work-up and/or purification procedure.
  • the different sub-steps of the two or three step variants of step (ii) can be performed in the presence of the same catalyst or in the presence of different catalysts. If the same catalyst is applied in the sub-steps, the course of the reaction is typically controlled via the reaction temperature, the removal of volatile reaction products, such as the alcohol R 4 -OH, and/or the amount of the catalyst in the reaction. If different catalysts are applied in the sub-steps, the first sub-step, i.e. the formation of the acetal intermediate (II), is typically performed with a first catalyst, e.g. a Br ⁇ nsted acid, and the following sub-steps are performed with a second catalyst different from the first catalyst, e.g. a Lewis acid. If a second catalyst different from the first catalyst is applied in the following sub-steps, the first catalyst can be removed via extractive work-up and/or the second catalyst is added to the reaction mixture comprising the first catalyst.
  • a first catalyst e.g. a Br ⁇ nsted acid
  • Suitable catalysts that can be applied in the two or three step variant of step (ii) are the catalysts as defined above.
  • the catalyst applied in the first sub-step of the two or three step variant of step (ii) is preferably selected from weak to moderately strong Br ⁇ nsted acids, as defined above.
  • the vinylether compounds are selected from compounds (V), wherein R 4 is C 2 -C 4 -alkyl or 2-vinyloxyethyl, even more preferably ethyl, propyl, isobutyl or 2-vinyloxyethyl, even more preferably ethyl, propyl or isobutyl, in particular ethyl or isobutyl, especially ethyl.
  • step (ii) the 2,5,6-trimethylcyclohex-2-en-1-ol is directly converted to the desired aldehyde compounds of formula (I), wherein X represents a group X 1 .
  • Suitable catalysts that can be applied in the one step variant of step (ii) are the catalysts as defined above.
  • the reaction rate may be increased by using moderately strong Br ⁇ nsted acids and/or Lewis acids.
  • the catalyst is selected from moderately strong Br ⁇ nsted acids, such as phosphoric acid, phosphonic acids, such as methylphosphonic acid, ethylphosphonic acid, propylphosphonic acid or phenylphosphonic acid, oxalic acid, chloroacetic acid, and Lewis acids, such as Fe(III)acetylacetonate, Fe(II)acetylacetonate, Fe(II)acetate, Fe(II)triflate, Cu(II)acetylacetonate, Cu(II)acetate or Cu(II)triflate.
  • moderately strong Br ⁇ nsted acids such as phosphoric acid, phosphonic acids, such as methylphosphonic acid, ethylphosphonic acid, propylphosphonic acid or phenylphosphonic acid, oxalic acid, chloroacetic acid
  • Lewis acids such as Fe(III)acetylacet
  • the amount of catalyst used in the reaction in step (ii) is typically in the range of from 0.0001 to 0.5 equivalents, preferably in the range of from 0.0005 to 0.3 equivalents, in particular in the range of from 0.001 to 0.1 equivalents based on 1 equivalent of the compound (IV).
  • the ratio of the compound (IV) to the vinylether of the general formula (V) applied in the reaction in step (ii) varies within a brought range.
  • the ratio of the compound (IV) to the vinylether of the general formula (V) applied in the reaction in step (ii) is typically in the range of from 1:1 to 1:20, preferably in the range of from 1:1.1 to 1:15, more preferably in the range of from 1:1.2 to 1:10, in particular in the range of from 1:1.5 to 1:5.
  • the reaction in step (ii) can be carried out in the presence of an inert solvent, as defined above, or in the absence of any external solvent.
  • the reaction in step (ii) is carried out in the absence of any external solvent.
  • the applied vinylether compound (V) acts as internal solvent.
  • the first sub-step i.e. the formation of the acetal intermediates (II) is preferably performed at a reaction temperature in the range of from 10 to 100°C, in particular in the range of from 20 to 70°C.
  • the following sub-steps i.e. the further conversion of the acetal intermediates (II) to the vinylether intermediates (III) and/or the compound (I), wherein X represents a group X 1 , are preferably performed at a reaction temperature in the range of from 90 to 250°C, more preferably in the range of from 100 to 220°C, in particular in the range of from 110 to 200°C.
  • the reaction in step (ii) is preferably performed at a reaction temperature in the range of from 90 to 250°C, more preferably in the range of from 110 to 240°C, in particular in the range of from 120 to 230°C.
  • the reaction in step (ii) can take place in the absence of or in the presence of an inert gas.
  • inert gas generally means a gas, which under the prevailing reaction conditions does not enter into any reactions with the starting materials, reagents, or solvents participating in the reaction, or with the resultant products.
  • the inert gas is preferably selected from argon and nitrogen as well as mixtures thereof, in particular the inert gas is nitrogen.
  • the reaction in step (ii) may be carried out at atmospheric pressure or at elevated pressures.
  • the reaction in step (ii) is preferably carried out at elevated pressures, more preferably at a pressure in the range from 1.1 to 20 bar, in particular at a pressure in the range from 1.5 to 15 bar.
  • the reaction in step (ii) is preferably carried out at atmospheric pressure.
  • step (ii) of the process of the present invention comprises the following steps:
  • step (ii.a), the preferable ratios and amounts of the reactants (IV) and (V), the preferable amount of the catalyst as well as the preferable reaction conditions applied in step (ii.a) are as defined above for the first sub-step of the two or three step variant of step (ii).
  • the catalysts applied in steps (ii.b) and (ii.c), the preferable amounts of the catalysts and the preferable reaction conditions applied in steps (ii.b) and (ii.c) are as defined above for the further sub-step(s) of the two or three step variant of step (ii).
  • step (ii.b) can be performed at temperatures of at least 150°C, preferably at temperatures in the range of from 150 to 300°C, in particular in the range of from 150 to 260°C, alternatively or in addition to the application of a catalyst.
  • reaction of step (ii.c) can be performed at temperatures of at least 150°C, preferably at temperatures in the range of from 150 to 280°C, in particular in the range of from 155 to 250°C, alternatively or in addition to the application of a catalyst.
  • the first intermediate compound of the general formula (II) may also react directly to the final aldehyde compound of the general formula (I), wherein X represents the group X 1 .
  • step (ii) of the process of the present invention comprises the following steps:
  • step (ii) the catalyst applied in step (ii.a'), the preferable ratios and amounts of the reactants (IV) and (V), the preferable amount of the catalyst as well as the preferable reaction conditions applied in step (ii.a') are as defined above for the first sub-step of the two or three step variant of step (ii).
  • step (ii.b') the catalysts applied in step (ii.b'), the preferable amounts of the catalysts and the preferable reaction conditions applied in step (ii.b') are as defined above for the further sub-step(s) of the two or three step variant of step (ii).
  • the reaction of step (ii.b') can be performed at temperatures of at least 160°C, preferably at temperatures in the range of from 160 to 300°C, in particular in the range of from 165 to 260°C, alternatively or in addition to the application of a catalyst.
  • the reaction in step (ii) is performed in a microwave heating apparatus.
  • the catalyst is preferably selected from soft Lewis acids, in particular from Cu(II)acetate, Cu(I)acetate and Fe(III)acetylacetonate.
  • the reaction in the microwave heating apparatus is preferably conducted at a reaction temperature in the range of from 150 to 260°C, in particular in the range of from 170 to 240°C.
  • step (iii) of the process of the present invention the aldehyde compound obtained in step (ii) is subjected to a selective reduction reaction of the carbonyl group to a hydroxyl group, to obtain a compound of the general formula (I), wherein X represents a group X 2 where R 1 is hydrogen.
  • Suitable reducing agents and reaction conditions are for example described above in connection with the chemoselective reduction of 2,5,6-trimethylcyclohex-2-en-1-one (VI) to 2,5,6-trimethylcyclohex-2-en-1-ol (IV).
  • the selective reduction of the aldehyde group may also be achieved by reacting the compound obtained in step (ii) with hydrogen in the presence of a transition metal catalyst, e.g. by analogy to the method described in EP 71787 .
  • step (iv.a) of the process of the present invention the compound obtained in step (iii) is reacted with an alkylation reagent R 1a -Y, wherein R 1a is methyl or ethyl and Y represents a leaving group, selected from halogen, such as Cl, Br or I, and sulfonates, such as tosylate, mesylate, triflate or nonaflate, in the presence of a base, to obtain a compound of the general formula (I), wherein X represents a group X 2 where R 1 is methyl or ethyl.
  • R 1a is methyl or ethyl
  • Y represents a leaving group, selected from halogen, such as Cl, Br or I
  • sulfonates such as tosylate, mesylate, triflate or nonaflate
  • Suitable bases are typically selected from inorganic bases and organic bases.
  • Suitable inorganic bases that can be used in this alkylation reaction are for example alkali metal carbonates, e.g. Li 2 CO 3 , Na 2 CO 3 , K 2 CO 3 or Cs 2 CO 3 , alkali metal hydroxides, e.g. LiOH, NaOH or KOH, and hydride donors, e.g. NaH, LiAlH 4 , NaBH 4 , metallic Na or metallic K.
  • alkali metal carbonates e.g. Li 2 CO 3 , Na 2 CO 3 , K 2 CO 3 or Cs 2 CO 3
  • alkali metal hydroxides e.g. LiOH, NaOH or KOH
  • hydride donors e.g. NaH, LiAlH 4 , NaBH 4 , metallic Na or metallic K.
  • Suitable organic bases that can be used in this alkylation reaction are for example tertiary amines, e.g. trimethylamine, triethylamine, tripropylamine, ethyldiisopropylamine and the like, or basic N-heterocycles, such as morpholine, pyridine, lutidine, DMAP, DABCO, DBU or DBN.
  • tertiary amines e.g. trimethylamine, triethylamine, tripropylamine, ethyldiisopropylamine and the like
  • basic N-heterocycles such as morpholine, pyridine, lutidine, DMAP, DABCO, DBU or DBN.
  • the alkylation reaction is performed under conventional alkylation reaction conditions that are well known to the skilled person.
  • step (iv.b) of the process of the present invention the compound obtained in step (iii) is reacted with a C 1 -C 3 -carboxylic acid or a C 2 -C 3 -carboxylic acid anhydride in the presence of an esterification catalyst, or with a C 2 -C 3 -carboxylic acid chloride in the presence of a base, to obtain a compound of the general formula (I), wherein X represents a group X 3 .
  • the C 1 -C 3 -carboxylic acid used in step (iv.b) of the process of the present invention is formic acid, acetic acid or propionic acid.
  • the C 2 -C 3 -carboxylic acid anhydride used in step (iv.b) of the process of the present invention is acetic anhydride or propionic anhydride.
  • the C 2 -C 3 -carboxylic acid chloride used in step (iv.b) of the process of the present invention is acetic acid chloride or propionic acid chloride.
  • Suitable bases are preferably selected from organic bases.
  • Suitable organic bases that can be used are for example tertiary amines, e.g. trimethylamine, triethylamine, tripropylamine, ethyldiisopropylamine and the like, or basic N-heterocycles, such as morpholine, pyridine, lutidine, DMAP, DABCO, DBU or DBN.
  • Suitable esterification catalysts that can be applied in this reaction are well known to the skilled person.
  • Suitable esterification catalysts are for example metal based catalysts, e.g. iron, cadmium, cobalt, lead, zinc, antimony, magnesium, titanium and tin catalysts in the form of metals, metal oxides or metal salts, such as metal alcoxylates; mineral acids, such as sulfuric acid, hydrochloric acid or phosphoric acid; or organic sulfonic acids, such as methane sulfonic acid or para-toluene sulfonic acid.
  • metal based catalysts e.g. iron, cadmium, cobalt, lead, zinc, antimony, magnesium, titanium and tin catalysts in the form of metals, metal oxides or metal salts, such as metal alcoxylates
  • mineral acids such as sulfuric acid, hydrochloric acid or phosphoric acid
  • organic sulfonic acids such as methane sulfonic acid or
  • step (iv.c) is typically performed in the presence of a catalyst, i.e. a transesterification catalyst.
  • a catalyst i.e. a transesterification catalyst.
  • Suitable trans-carbonylation catalysts are for example the catalysts mentioned above in connection with the esterification reaction in step (iv.b).
  • step (iv.c) is typically performed in the presence of a catalyst, i.e. an alkoxycarbonylation catalyst.
  • a catalyst i.e. an alkoxycarbonylation catalyst.
  • alkoxycarbonylation catalysts are for example Lewis acids, such as BiCl 3 or Zn(OAc) 2 , phosphines, such as triphenylphosphine or tetrabromomethane.
  • the reaction in step (iv.c) is typically performed in the presence of a base.
  • Suitable bases are preferably selected from organic bases, as defined above.
  • reaction conditions for the preparation of the carbonate compounds of the general formula (I), wherein X represents a group X 4 are well known to the skilled person. Suitable reaction conditions and protocols are for example described in "Homogeneous Carbonylation Reactions in the Synthesis of Compounds of Pharmaceutical Importance", by Rita Skoda-Földes, Chapter 12: “Alkoxycarbonylation of Alcohols and Phenols", and the references cited therein.
  • the reaction mixtures obtained in steps (i), (ii), (ii.a), (ii.b), (ii.c), (ii.a'), (ii.b'), (iii), (iv.a), (iv.b) and/or (iv.c) are worked up in a customary manner, for example by mixing with water and neutralizing the reaction mixture, if acids, such as Lewis acids, bases and/or metal organic reagents were applied in the reactions, separating the phases, isolating the product from the organic phases and, if appropriate, purifying the crude products by usual methods, e.g. by distillative, extractive or chromatographic methods.
  • a heterogeneous catalyst e.g. a supported Lewis-acid catalyst or a heterogeneous hydration catalyst, the catalyst is typically filtered off prior to work up.
  • the compounds of formulae (I), (II), (III) or (IV) or a mixture of two or more compounds of the formulae (I), (II), (III) and (IV), or a stereoisomer thereof or a mixture of two or more stereoisomers thereof, as defined above, are useful as aroma chemicals.
  • a further aspect of the present invention is the use of a compound of formulae (I), (II), (III) or (IV) or of a mixture of two or more compounds of the formulae (I), (II), (III) and (IV), or of a stereoisomer thereof or of a mixture of two or more stereoisomers thereof, as defined above, as an aroma chemical.
  • the present invention relates to the use of a compound of formulae (I), (II) or (III) or of a mixture of two or more compounds of the formulae (I), (II) and (III), or of a stereoisomer thereof or of a mixture of two or more stereoisomers thereof, as defined above, as an aroma chemical.
  • aroma refers to a sensory property and comprises an odor and/or a flavor.
  • aroma chemical denotes a substance which is used to obtain a sensory impression, to be more precise an olfactory or flavor impression, in particular a fragrance or flavor impression.
  • olfactory denotes an odor impression without any positive or negative judgement, while the term “fragrance” (also termed “perfume” or “scent”) is connected to an odor impression which is generally felt as pleasant. A flavor induces a taste impression.
  • aroma profile denotes the overall aroma impression of an aroma chemical and is composed of the individual aroma impressions of an aroma chemical.
  • aroma composition refers to a composition which induces an aroma.
  • aroma composition comprises "odor composition” and/or "flavor composition”.
  • An odor composition being a composition, which predominately induces an odor impression
  • a flavor composition being a composition, which predominantly induces a taste impression.
  • odor composition comprises "fragrance composition” or “scent composition” (used interchangeably herein), which predominately induce an odor impression which is generally felt as pleasant.
  • substantially describes the interaction of an aroma chemical with a surface, such as for example the skin or a textile, especially after subsequent treatment of the surface, such as for example washing.
  • the substantivity can for example be determined by washing a textile with a textile detergent composition comprising the aroma chemical and subsequent olfactory evaluation of the textile directly after washing (wet textile) as well as evaluation of the dry textile after prolonged storage.
  • Stability describes the behavior of an aroma chemical upon contact with oxygen, light and/or other substances.
  • An aroma chemical with high stability maintains its aroma profile over a long period in time, preferably in a large variety of compositions and under various storage conditions.
  • “Pleasant odor”, “pleasant odor impression”, “pleasant odiferous properties” are hedonistic expressions which describe the niceness and conciseness of an odor impression conveyed by an aroma chemical.
  • the more general hedonistic expressions "advantageous sensory properties” or “advantageous organoleptic properties” describe the niceness and conciseness of an organoleptic impression conveyed by an aroma chemical.
  • “Niceness” and “conciseness” are terms which are familiar to the person skilled in the art, a perfumer. Niceness generally refers to a spontaneously brought about, positively perceived, pleasant sensory impression. However, “nice” does not have to be synonymous with “sweet”.
  • “Nice” can also be the odor of musk or sandalwood.
  • “Conciseness” generally refers to a spontaneously brought about sensory impression which - for the same test panel - brings about a reproducibly identical reminder of something specific.
  • a substance can have an odor which is spontaneously pronounced of that of an "apple”: the odor would then be concisely of "apples”. If this apple odor were very pleasant because the odor is reminiscent, for example, of a sweet, fully ripe apple, the odor would be termed “nice”.
  • the odor of a typically tart apple can also be concise. If both reactions arise upon smelling the substance, in the example thus a nice and concise apple odor, then this substance has particularly advantageous sensory properties.
  • odor-intensive substances refers to substances or aroma chemicals exhibiting intense odor impressions. Intense odor impressions are to be understood as meaning those properties of aroma chemicals which permit a striking perception even in very low gas space concentrations.
  • the intensity can be determined via a threshold value determination.
  • a threshold value is the concentration of a substance in the relevant gas space at which an odor impression can just still be perceived by a representative test panel, although it no longer has to be defined.
  • a substance class which probably belongs to the most odor-intensive known substance classes, i.e. has very low odor threshold values, are thiols, whose threshold value is often in the ppb/m 3 range.
  • the compounds of formulae (I), (II), (III) or (IV) or a mixture of two or more compounds of the formulae (I), (II), (III) and (IV), or a stereoisomer thereof or a mixture of two or more stereoisomers thereof, as defined above, are used as a fragrance.
  • the compounds of formulae (I), (II) or (III) or a mixture of two or more compounds of the formulae (I), (II) and (III), or a stereoisomer thereof or a mixture of two or more stereoisomers thereof, as defined above, are used as a fragrance.
  • 2-(2,4,5-trimethylcyclohex-2-en-1-yl)acetaldehyde is used to impart a green, watery, chrysanthema, grassy, aldehydic, lily of the valley, leathery, terpenic, and/or natural note. Since 2-(2,4,5-trimethylcyclohex-2-en-1-yl)acetaldehyde has a prominent lily of the valley odor note, 2-(2,4,5-trimethylcyclohex-2-en-1-yl)acetaldehyde can especially be used to impart a lily of the valley note. Thus, a particular embodiment of the invention relates to the use of 2-(2,4,5-trimethylcyclohex-2-en-1-yl)acetaldehyde to impart a lily of the valley note.
  • 6-(1-ethoxyethoxy)-1,4,5-trimethylcyclohex-1-ene is used to impart a watermelon, watery, green, almond, foodlike and technical note.
  • the intermediate (IV) i.e. 2,5,6-trimethyl-cyclohex-2-en-1-ol
  • the intermediate (IV) is used to impart an animalic, indole, technical, solvent, punguent and/or phenolic note.
  • concentrations of 100 ppm in ethanol however, 2,5,6-tri-methylcyclohex-2-en-1-ol, imparts a phenolic, green banana, nutty, milky and/or warm note.
  • 2,5,6-trimethylcyclohex-2-en-1-ol is used to imparts a phenolic, green banana, nutty, milky and/or warm note.
  • the compounds of formulae (I), (II), (III) or (IV) or a mixture of two or more compounds of the formulae (I), (II), (III) and (IV), or a stereoisomer thereof or a mixture of two or more stereoisomers thereof, as defined above, are used in a composition selected from the group consisting of perfume compositions, body care compositions (including cosmetic compositions and products for oral and dental hygiene), hygiene articles, cleaning compositions (including dishwashing compositions), textile detergent compositions, compositions for scent dispensers, foods, food supplements, pharmaceutical compositions and crop protection compositions.
  • the compounds of formulae (I), (II), (III) or (IV) or a mixture of two or more compounds of the formulae (I), (II), (III) and (IV), or a stereoisomer thereof or a mixture of two or more stereoisomers thereof are used as an aroma chemical, preferably as a fragrance, in the above compositions.
  • 2-(2,4,5-trimethylcyclohex-2-en-1-yl)acetaldehyde is used to impart a green, watery, chrysanthema, grassy, aldehydic, lily of the valley, leathery, terpenic, and/or natural note, especially a lily of the valley note, to the above-listed compositions.
  • 6-(1-ethoxyethoxy)-1,4,5-trimethylcyclohex-1-ene is used to impart a watermelon, watery, green, almond, foodlike and technical note to the above-listed compositions.
  • 2,5,6-trimethylcyclohex-2-en-1-ol is used to impart an animalic, indole, technical, solvent, punguent and/or phenolic note to the above-listed compositions.
  • 2,5,6-trimethylcyclohex-2-en-1-ol imparts a phenolic, green banana, nutty, milky and/or warm note to the above-listed compositions.
  • another aspect of the invention relates to the use of a compound of formulae (I), (II), (III) or (IV) or of a mixture of two or more compounds of the formulae (I), (II), (III) and (IV), or of a stereoisomer thereof or of a mixture of two or more stereoisomers thereof, as defined above, for modifying the scent character of a fragranced composition.
  • the compounds of formulae (I), (II), (III) or (IV) or a mixture of two or more compounds of the general formulae (I), (II), (III) and (IV), or a stereoisomer thereof or a mixture of two or more stereoisomers thereof exhibit advantageous secondary properties.
  • another aspect of the invention relates to the use of a compound of formulae (I), (II), (III) or (IV) or mixtures of two or more compounds of formulae (I), (II), (III) and (IV), or a stereoisomer thereof or a mixtures of stereoisomers thereof as a booster for other fragrances.
  • Booster effect means that the substances enhance and intensify in perfumery formulations the overall impression of the mixture.
  • Menthyl methyl ether intensifies the perfumery or taste mixtures of peppermint oils and particularly in top notes brings about a considerably more intensive and more complex perception although the ether itself, being a pure substance, develops no particular intensive odor at all.
  • Hedione® methyl dihydrojasmonate
  • Booster effects are particularly desired when top-note-characterized applications are required, in which the odor impression is to be conveyed particularly quickly and intensively, for example in deodorants, air fresheners or in the taste sector in chewing gums.
  • the compounds of formulae (I), (II), (III) or (IV) or a mixture of two or more compounds of the formulae (I), (II), (III) and (IV), or a stereoisomer thereof or a mixture of two or more stereoisomers thereof are generally used in an overall amount of 0.1 to 20% by weight, preferably in an amount of 0.5 to 5% by weight, in particular in an amount of from 0.6 to 3% by weight, based on the total weight of the fragrance mixture.
  • the compounds of formulae (I), (II), (III) or (IV) or a mixture of two or more compounds of the formulae (I), (II), (III) and (IV), or a stereoisomer thereof or a mixture of two or more stereoisomers thereof can have further positive effects on the composition in which they are used. For example, they can enhance the overall performance of the composition into which they are incorporated, such as the stability, e.g. the formulation stability, the extendability or the substantivity of the composition.
  • the present invention relates to a composition
  • a composition comprising a compound of formulae (I), (II), (III) or (IV) or a mixture of two or more compounds of the formulae (I), (II), (III) and (IV), or of a stereoisomer thereof or of a mixture of two or more stereoisomers thereof.
  • the composition comprises
  • the composition describe herein comprises a compound of formulae (I), (II) or (III) or a mixture of two or more compounds of the formulae (I), (II) and (III), or of a stereoisomer thereof or of a mixture of two or more stereoisomers thereof.
  • a preferred embodiment of the invention relates to a composition
  • a composition comprising
  • the further aroma chemical is of course different from the compounds of formulae (I), (II), (III) or (IV), if present, or the stereoisomers thereof.
  • the compounds of formulae (I), (II), (III) or (IV) or a mixture of two or more compounds of the formulae (I), (II), (III) and (IV), or a stereoisomer thereof or a mixture of two or more stereoisomers thereof have particularly good, virtually universal solvent properties for and in aroma chemicals and other customary ingredients in compositions such as, in particular, fragrance compositions. Therefore, they are well combinable with aroma chemicals, allowing, in particular, the creation of aroma compositions, in particular fragrance compositions, having novel advantageous sensory profiles. Furthermore, as already explained above, they can provide a booster effect for other fragrances.
  • the composition comprises a compound of formulae (I), (II), (III) or (IV) or a mixture of two or more compounds of the formulae (I), (II), (III) and (IV), or of a stereoisomer thereof or of a mixture of two or more stereoisomers thereof, as defined above; and at least one further aroma chemical.
  • the composition comprises a compound of formulae (I), (II) or (III) or a mixture of two or more compounds of the formulae (I), (II) and (III), or of a stereoisomer thereof or of a mixture of two or more stereoisomers thereof, as defined above; and at least one further aroma chemical.
  • the further aroma chemical can for example be one, preferably 2, 3, 4, 5, 6, 7, 8 or further aroma chemicals, selected from the group consisting of: Geranyl acetate (3,7-Dimethyl-2,6 octadien-1yl acetate), alpha-hexylcinnamaldehyde, 2-phenoxyethyl isobutyrate (Phenirat 1 ), dihydromyrcenol (2,6-dimethyl-7-octen-2-ol), methyl dihydrojasmonate (preferably with a content of cis isomer of more than 60% by weight) (Hedione 9 , Hedione HC 9 ), 4,6,6,7,8,8-hexamethyl-1,3,4,6,7,8-hexahydro-cyclopenta[g]benzopyran (Galaxolid 3 ), tetrahydrolinalool (3,7-dimethyloctan-3-ol), ethyl-linalool,
  • the aforementioned aroma chemical(s) are accordingly preferably combined with the compound of formulae (I), (II), (III) or (IV) or a mixture of two or more compounds of formulae (I), (II), (III), and (IV), or a stereoisomer thereof or a mixture of stereoisomers thereof, as defined above.
  • a preferred embodiment of the invention relates to a composition
  • a composition comprising a compound of formulae (I), (II), (III) or (IV) or a mixture of two or more compounds of the formulae (I), (II), (III) and (IV), or of a stereoisomer thereof or of a mixture of two or more stereoisomers thereof, as defined above, and at least one further aroma chemical selected from the group consisting of methyl benzoate, benzyl acetate, geranyl acetate, 2-isobutyl-4-methyltetrahydro-2H-pyran-4-ol, linalool, 2-isobutyl-4-methyltetrahydro-2H-pyran-4-ol and methyl benzoate.
  • a preferred embodiment of the invention relates to a composition
  • a composition comprising a compound of formulae (I), (II), (III) or (IV) or a mixture of two or more compounds of the formulae (I), (II), (III) and (IV), or of a stereoisomer thereof or of a mixture of two or more stereoisomers thereof, as defined above, and at least one further aroma chemical selected from the group consisting of ethylvanillin, vanillin, 2,5-dimethyl-4-hydroxy-2H-furan-3-one (furaneol) or 3-hydroxy-2-methyl-4H-pyran-4-one (maltol).
  • the at least one non-aroma chemical carrier can be a compound, a mixture of compounds or other additives, which have no or no noteworthy sensory properties.
  • the at least one non-aroma chemical carrier if present in the compositions according to the present invention, is a compound, a mixture of compounds or other additives, which have no or no noteworthy sensory properties.
  • the non-aroma chemical carrier serves for the dilution and/or the fixing of the aroma chemical(s), i.e. the compounds of formulae (I), (II), (III) or (IV) and optionally one or more further aroma chemical different from compounds (I), (II), (III) and (IV), as defined above, comprised in the composition.
  • Suitable carrier materials can be liquid or oil-like carrier materials as well as wax-like or solid carrier materials.
  • the non-aroma chemical carrier if present in the compositions according to the present invention, is selected from the group consisting of surfactants, oil components and solvents.
  • a further aspect of the invention is directed to a composition
  • a composition comprising the compounds of formulae (I), (II), (III) or (IV) or a mixture of two or more compounds of the formulae (I), (II), (III) and (IV), or a stereoisomer thereof or a mixture of two or more stereoisomers thereof, as defined above, and at least one further component selected from the group consisting of aroma chemicals, as defined above, surfactants, emollients (oil component), solvents, anti-oxidants and deodorant-active agents.
  • compositions comprising a compound of formulae (I), (II), (III) or (IV) or a mixture of two or more compounds of the formulae (I), (II), (III) and (IV), or a stereoisomer thereof or a mixture of two or more stereoisomers thereof, as defined above, and at least one further component selected from the group consisting of surfactants, emollients (oil component), solvents, anti-oxidants and deodorant-active agents.
  • compositions comprising a compound of formulae (I), (II), (III) or (IV) or a mixture of two or more compounds of the formulae (I), (II), (III) and (IV), or a stereoisomer thereof or a mixture of two or more stereoisomers thereof, as defined above, and at least one further component selected from the group consisting of emollients (oil component), solvents, anti-oxidants and deodorant-active agents.
  • compositions described above and below comprise a compound of formulae (I), (II) or (III) or a mixture of two or more compounds of the formulae (I), (II) and (III), or of a stereoisomer thereof or of a mixture of two or more stereoisomers thereof.
  • One embodiment of the invention is directed to a composition
  • a composition comprising a compound of formulae (I), (II), (III) or (IV) or a mixture of two or more compounds of the formulae (I), (II), (III) and (IV), or a stereoisomer thereof or a mixture of two or more stereoisomers thereof, as defined above, and at least one solvent.
  • a “solvent” serves for the dilution of the compounds of formulae (I), (II), (III) or (IV) or a mixture of two or more compounds of the formulae (I), (II), (III) and (IV), or a stereoisomer thereof or a mixture of two or more stereoisomers thereof, as defined above, to be used according to the invention and/or any further component of the composition without having its own aroma.
  • the one or more solvent(s) can be present in the composition from 0.01 to 99% by weight based on the composition.
  • the composition comprise 0.1 to 90 weight%, preferably 0.5 to 80 weight% of solvent(s) based on the composition.
  • the amount of solvent(s) can be chosen depending on the composition.
  • the composition comprises 0.05 to 10 weight%, preferably 0.1 to 5 weight%, more preferably 0.2 to 3 weight% based on the composition.
  • the composition comprises 20 to 70 weight%, preferably 25 to 50 weight% of solvent(s) based on the composition.
  • Preferred solvents are ethanol, dipropylene glycol (DPG), propylene glycol, 1,2-butylene glycol, glycerol, diethylene glycol monoethyl ether, diethyl phthalate (DEP), isopropyl myristate (IPM), triethyl citrate (TEC), and benzyl benzoate (BB).
  • DPG dipropylene glycol
  • PEP diethyl phthalate
  • IPM isopropyl myristate
  • TEC triethyl citrate
  • BB benzyl benzoate
  • Especially preferred solvents are selected from the group consisting of ethanol, propylene glycol, dipropylene glycol, triethyl citrate, benzyl benzoate and isopropyl myristate.
  • the solvent is selected from the group consisting of ethanol, isopropanol, diethylene glycol monoethyl ether, glycerol, propylene glycol, 1,2-butylene glycol, dipropylene glycol, triethyl citrate and isopropyl myristate.
  • One embodiment of the invention is directed to a composition
  • a composition comprising a compound of formulae (I), (II), (III) or (IV) or a mixture of two or more compounds of formulae (I), (II), (III) and (IV), or a stereoisomer thereof or a mixture of stereoisomers thereof, as defined above, and at least one anti-oxidant.
  • Anti-oxidants are able to inhibit or prevent the undesired changes in the compositions to be protected caused by oxygen effects and other oxidative processes.
  • the effect of the anti-oxidants consists in most cases in them acting as free-radical scavengers for the free radicals which arise during autoxidation.
  • Anti-oxidants can for example be selected from the group consisting of
  • the anti-oxidant is selected from the group consisting of pentaerythrityl, tetra-di-t-butyl hydroxyhydrocinnamate, nordihydroguaiaretic acid, ferulic acid, resveratrol, propyl gallate, butylhydroxytoluene (BHT), butylhydroxyanisole (BHA), ascorbyl palmitate and tocopherol.
  • compositions according to the invention can comprise the anti-oxidants in an amount of 0.001 to 25 wt.-%, preferably 0.005 to 10 wt.-%, preferably 0.01 to 8 wt.-%, preferably 0.025 to 7 wt.-%, preferably 0.05 to 5 wt.-%, based on the total weight of the composition.
  • the compounds of formulae (I), (II), (III) or (IV) or a mixture of two or more compounds of the formulae (I), (II), (III) and (IV), or a stereoisomer thereof or a mixture of two or more stereoisomers thereof, as defined above, can also be used together with deodorizing compositions.
  • Deodorizing compositions counteract, mask or eliminate body odors.
  • Body odors are formed through the action of skin bacteria on apocrine perspiration which results in the formation of unpleasant-smelling degradation products.
  • One embodiment of the invention is therefore directed to a composition
  • a composition comprising a compound of formulae (I), (II), (III) or (IV) or a mixture of two or more compounds of the formulae (I), (II), (III) and (IV), or a stereoisomer thereof or a mixture of two or more stereoisomers thereof, as defined above, and at least one deodorant-active agent.
  • the at least one deodorant-active agent is selected from the groups consisting of anti-perspirants, esterase inhibitors and antibacterial agents.
  • Suitable antiperspirants can be selected from the group consisting of salts of aluminium, zirconium or zinc.
  • Examples are aluminium chloride, aluminium chlorohydrate, aluminium dichlorohydrate, aluminium sesquichlorohydrate and complex compounds thereof, for example with 1,2-propylene glycol, aluminium hydroxyallantoinate, aluminium chloride tartrate, aluminium zirconium trichlorohydrate, aluminium zirconium tetrachlorohydrate, aluminium zirconium pentachlorohydrate and complex compounds thereof, for example with amino acids, such as glycine.
  • Aluminium chlorohydrate, aluminium zirconium tetrachlorohydrate, aluminium zirconium pentachlorohydrate and complex compounds thereof are preferably used.
  • compositions comprise at least one antiperspirant selected from the group consisting aluminium chloride, aluminium chlorohydrate, aluminium dichlorohydrate, aluminium sesquichlorohydrate, aluminium hydroxyallantoinate, aluminium chloride tartrate, aluminium zirconium trichlorohydrate, aluminium zirconium tetrachlorohydrate and aluminium zirconium pentachlorohydrate
  • compositions according to the invention can comprise the antiperspirants in an amount of 1 to 50, preferably 5 to 30 and more particularly 10 to 25 wt.-%, based on the solids content of the composition.
  • esterase inhibitors are for example trialkyl citrates, such as trimethyl citrate, tripropyl citrate, triisopropyl citrate, tributyl citrate and, in particular, triethyl citrate.
  • Esterase inhibitors inhibit enzyme activity and thus reduce odor formation. The free acid is probably released by the cleavage of the citric acid ester and reduces the pH value of the skin to such an extent that the enzymes are inactivated by acylation.
  • esterase inhibitors are sterol sulfates or phosphates such as, for example, lanosterol, cholesterol, campesterol, stigmasterol and sitosterol sulfate or phosphate, dicarboxylic acids and esters thereof, for example glutaric acid, glutaric acid monoethyl ester, glutaric acid diethyl ester, adipic acid, adipic acid monoethyl ester, adipic acid diethyl ester, malonic acid and malonic acid diethyl ester, hydroxycarboxylic acids and esters thereof, for example citric acid, malic acid, tartaric acid or tartaric acid diethyl ester, and zinc glycinate.
  • dicarboxylic acids and esters thereof for example glutaric acid, glutaric acid monoethyl ester, glutaric acid diethyl ester, adipic acid, adipic acid monoethyl ester, adipic acid dieth
  • compositions comprise at least one esterase inhibitor selected from the group consisting of trimethyl citrate, tripropyl citrate, triisopropyl citrate, tributyl citrate triethyl citrate, lanosterol, cholesterol, campesterol, stigmasterol, sitosterol sulfate, sitosterol phosphate, glutaric acid, glutaric acid monoethyl ester, glutaric acid diethyl ester, adipic acid, adipic acid monoethyl ester, adipic acid diethyl ester, malonic acid, malonic acid diethyl ester, citric acid, malic acid, tartaric acid, tartaric acid diethyl ester and zinc glycinate.
  • esterase inhibitor selected from the group consisting of trimethyl citrate, tripropyl citrate, triisopropyl citrate, tributyl citrate triethyl citrate, lanosterol, cholesterol, campesterol, stigmasterol,
  • compositions according to the invention can comprise the esterase inhibitors in amounts of 0.01 to 20, preferably 0.1 to 10 and more particularly 0.5 to 5 wt.-%, based on the solids content of the composition.
  • anti-bacterial agents encompasses substances which have bactericidal and/or bacteriostatic properties. Typically these substances act against gram-positive bacteria such as, for example, 4-hydroxybenzoic acid and salts and esters thereof, N-(4-chlorophenyl)-N'-(3,4-dichlorophenyl)-urea, 2,4,4'-trichloro-2'-hydroxydiphenylether (triclosan), 4-chloro-3,5-dimethylphenol, 2,2'-methylene-bis-(6-bromo-4-chlorophenol), 3-methyl-4-(1-methylethyl)-phenol, 2-benzyl-4-chlorophenol, 3-(4-chlorophenoxy)-propane-1,2-diol, 3-iodo-2-propinyl butyl carbamate, chlorhexidine, 3,4,4'-trichlorocarbanilide (TTC), phenoxyethanol, glycerol monocaprate
  • the antibacterial agent is selected from the group consisting of chitosan, phenoxyethanol, 5-Chloro-2-(2,4-dichlorophenoxy)-phenol, 4-hydroxybenzoic acid and salts and esters thereof, N-(4-chlorophenyl)-N'-(3,4-dichlorophenyl)-urea, 2,4,4'-trichloro-2'-hydroxydiphenylether (triclosan), 4-chloro-3,5-dimethylphenol, 2,2'-methylene-bis-(6-bromo-4-chlorophenol), 3-methyl-4-(1-methylethyl)-phenol, 2-benzyl-4-chlorophenol, 3-(4-chlorophenoxy)-propane-1,2-diol, 3-iodo-2-propinyl butyl carbamate, chlorhexidine, 3,4,4'-trichlorocarbanilide (TTC), phenoxyethanol, glycerol monocaprate,
  • compositions according to the invention can comprise the antibacterial agents in amounts of 0.01 to 5 wt.% and preferably 0.1 to 2 wt.-%, based on the solids content of the composition.
  • the compounds of formulae (I), (II), (III) or (IV) or a mixture of two or more compounds of the formulae (I), (II), (III) and (IV), or a stereoisomer thereof or a mixture of two or more stereoisomers thereof are suitable for use in surfactant-containing compositions. According to their characteristic scent profiles, they can especially be used for the perfuming of surfactant-containing compositions such as, for example, cleaners (in particular laundry care products and all-purpose cleaners).
  • compositions according to the invention can thus preferably comprise at least one surfactant.
  • the surfactant(s) may be selected from anionic, non-ionic, cationic and/or amphoteric or zwitterionic surfactants.
  • Surfactant-containing compositions such as for example shower gels, foam baths, shampoos, etc., preferably contain at least one anionic surfactant.
  • compositions according to the invention usually contain the surfactant(s), in the aggregate, in a quantity of 0 to 40% by weight, preferably 0 to 20% by weight, more preferably 0.1 to 15% by weight, and particularly 0.1 to 10% by weight, based on the total weight of the composition.
  • nonionic surfactants are fatty alcohol polyglycol ethers, alkylphenol polyglycol ethers, fatty acid polyglycol esters, fatty acid amide polyglycol ethers, fatty amine polyglycol ethers, alkoxylated triglycerides, mixed ethers and mixed formals, optionally partly oxidized alk(en)yl oligoglycosides or glucuronic acid derivatives, fatty acid-N-alkyl glucamides, protein hydrolyzates (particularly wheat-based vegetable products), polyol fatty acid esters, sugar esters, sorbitan esters, polysorbates and amine oxides. If the nonionic surfactants contain polyglycol ether chains, they may have a conventional homolog distribution, although they preferably have a narrow-range homolog distribution.
  • Zwitterionic surfactants are surface-active compounds which contain at least one quaternary ammonium group and at least one -COO (-) or -SO 3 (-) group in the molecule.
  • Particularly suitable zwitterionic surfactants are the so-called betaines, such as the N-alkyl-N,N-dimethyl ammonium glycinates, for example, cocoalkyl dimethyl ammonium glycinate, N-acylaminopropyl-N,N-dimethyl ammonium glycinates, for example, cocoacylaminopropyl dimethyl ammonium glycinate, and 2-alkyl-3-carboxymethyl-3-hydroxyethyl imidazolines, containing 8 to 18 carbon atoms in the alkyl or acyl group, and cocoacylaminoethyl hydroxyethyl carboxymethyl glycinate.
  • Ampholytic surfactants are also suitable, particularly as co-surfactants.
  • Ampholytic surfactants are surface-active compounds which, in addition to a C 8 to C 18 alkyl or acyl group, contain at least one free amino group and at least one -COOH- or -SO 3 H- group in the molecule and which are capable of forming inner salts.
  • ampholytic surfactants are N-alkyl glycines, N-alkyl propionic acids, N-alkylaminobutyric acids, N-alkyliminodipropionic acids, N-hydroxyethyl-N-alkylamidopropyl glycines, N-alkyl taurines, N-alkyl sarcosines, 2-alkylaminopropionic acids and alkylaminoacetic acids containing around 8 to 18 carbon atoms in the alkyl group.
  • Particularly preferred ampholytic surfactants are N-cocoalk-ylaminopropionate, cocoacylaminoethyl amino-propionate and acyl sarcosine.
  • Anionic surfactants are characterized by a water-solubilizing anionic group such as, for example, a carboxylate, sulfate, sulfonate or phosphate group and a lipophilic group. Dermatologically safe anionic surfactants are known to the practitioner in large numbers from relevant textbooks and are commercially available.
  • alkyl sulfates in the form of their alkali metal, ammonium or alkanolammonium salts
  • alkylether sulfates in the form of their alkali metal, ammonium or alkanolammonium salts
  • alkylether carboxylates acyl isethionates
  • acyl sarcosinates acyl taurines containing linear C 12 -C 18 alkyl or acyl groups
  • sulfosuccinates and acyl glutamates in the form of their alkali metal or ammonium salts.
  • Particularly suitable cationic surfactants are quaternary ammonium compounds, preferably ammonium halides, more especially chlorides and bromides, such as alkyl trimethyl ammonium chlorides, dialkyl dimethyl ammonium chlorides and trialkyl methyl ammonium chlorides, for example, cetyl trimethyl ammonium chloride, stearyl trim ethyl ammonium chloride, distearyl dimethyl ammonium chloride, lauryl dimethyl ammonium chloride, lauryl dimethyl benzyl ammonium chloride and tricetyl methyl ammonium chloride.
  • the readily biodegradable quaternary ester compounds such as, for example, the dialkyl ammonium methosulfates and methyl hydroxyalkyl dialkoyloxyalkyl ammonium methosulfates marketed under the name of Stepantexe and the corresponding products of the Dehyquart® series, may be used as cationic surfactants.
  • "Esterquats” are generally understood to be quaternized fatty acid triethanolamine ester salts. They can provide the compositions with particular softness. They are known substances which are prepared by the relevant methods of organic chemistry.
  • Other cationic surfactants suitable for use in accordance with the invention are the quaternized protein hydrolyzates.
  • One embodiment of the invention is directed to a composition
  • a composition comprising a compound of formulae (I), (II), (III) or (IV) or a mixture of two or more compounds of formulae (I), (II), (III) and (IV), or a stereoisomer thereof or a mixture of stereoisomers thereof, as defined above, and at least one oil component.
  • the oil components are typically present in a total quantity of 0.1 to 80, preferably 0.5 to 70, more preferably 1 to 60, even more preferably 1 to 50% by weight, in particular 1 to 40% by weight, more particularly 5 to 25% by weight and specifically 5 to 15% by weight based on the composition.
  • the oil components may be selected, for example, from Guerbet alcohols based on fatty alcohols containing 6 to 18 and preferably 8 to 10 carbon atoms and other additional esters, such as myristyl myristate, myristyl palmitate, myristyl stearate, myristyl isostearate, myristyl oleate, myristyl behenate, myristyl erucate, cetyl myristate, cetyl palmitate, cetyl stearate, cetyl isostearate, cetyl oleate, cetyl behenate, cetyl erucate, stearyl myristate, stearyl palmitate, stearyl stearate, stearyl isostearate, stearyl oleate, stearyl behenate, stearyl erucate, isostearyl myristate, isostearyl palmitate, isostearyl stearate
  • esters of C 18 -C 38 -alkyl-hydroxycarboxylic acids with linear or branched C 6 -C 22 -fatty alcohols are also suitable.
  • esters of C 18 -C 38 -alkyl-hydroxycarboxylic acids with linear or branched C 6 -C 22 -fatty alcohols are especially dioctyl malate, esters of linear and/or branched fatty acids with polyhydric alcohols (for example propylene glycol, dimer dial or trimer triol), triglycerides based on C 6 -C 10 -fatty acids, liquid mono-, di- and triglyceride mixtures based on C 6 -C 18 -fatty acids, esters of C 6 -C 22 -fatty alcohols and/or Guerbet alcohols with aromatic carboxylic acids, more particularly benzoic acid, esters of dicarboxylic acids with polyols containing 2 to 10 car- bon atoms and 2 to 6 hydroxyl groups, vegetable oils,
  • the compounds of formulae (I), (II), (III) or (IV) or a mixture of two or more compounds of the formulae (I), (II), (III) and (IV), or a stereoisomer thereof or a mixture of two or more stereoisomers thereof, as defined above, can be used in a wide range of aroma compositions.
  • the composition is an aroma composition, more preferably an odor composition, more preferably a fragrance composition.
  • composition according to the invention can be selected from, but is not limited to, the group consisting of perfume compositions, body care compositions, hygiene articles, cleaning compositions, textile detergent compositions, composition for scent dispensers, foods, food supplements, pharmaceutical compositions and crop protection compositions.
  • Non-limiting examples for body care composition are cosmetic compositions as well as products for oral and dental hygiene.
  • Non-limiting examples for cleaning composition are dishwashing compositions.
  • Perfume compositions can be selected from fine fragrances, air fresheners in liquid form, gel-like form or a form applied to a solid carrier, aerosol sprays, scented cleaners, perfume candles and oils, such as lamp oils or oils for massage.
  • Examples for fine fragrances are perfume extracts, Eau de perfumes, Eau de Toilettes, Eau de Colognes, Eau de Solide and Extrait perfume.
  • Body care compositions include cosmetic compositions and products for oral and dental hygiene, and can be selected from after-shaves, pre-shave products, splash colognes, solid and liquid soaps, shower gels, shampoos, shaving soaps, shaving foams, bath oils, cosmetic emulsions of the oil-in-water type, of the water-in-oil type and of the water-in-oil-in-water type, such as e.g. skin creams and lotions, face creams and lotions, sunscreen creams and lotions, after-sun creams and lotions, hand creams and lotions, foot creams and lotions, hair removal creams and lotions, after-shave creams and lotions, tanning creams and lotions, hair care products such as e.g.
  • hairsprays hair gels, setting hair lotions, hair conditioners, hair shampoo, permanent and semi-permanent hair colorants, hair shaping compositions such as cold waves and hair smoothing compositions, hair tonics, hair creams and hair lotions, deodorants and antiperspirants such as e.g. underarm sprays, roll-ons, deodorant sticks and deodorant creams, products of decorative cosmetics such as e.g. eye-liners, eye-shadows, nail varnishes, make-ups, lipsticks and mascara, and products for oral and dental hygiene, such as toothpaste, dental floss, mouth wash, breath fresheners, dental foam, dental gels and dental strips.
  • decorative cosmetics such as e.g. eye-liners, eye-shadows, nail varnishes, make-ups, lipsticks and mascara
  • products for oral and dental hygiene such as toothpaste, dental floss, mouth wash, breath fresheners, dental foam, dental gels and dental strips.
  • Hygiene articles can be selected from joss sticks, insecticides, repellents, propellants, rust removers, perfumed freshening wipes, armpit pads, baby diapers, sanitary towels, toilet paper, cosmetic wipes, pocket tissues, dishwasher and deodorizer.
  • Cleaning compositions such as e.g. cleaners for solid surfaces
  • perfumed acidic, alkaline and neutral cleaners such as e.g. floor cleaners, window cleaners, dishwashing detergents both for handwashing and machine washing use, bath and sanitary cleaners, scouring milk, solid and liquid toilet cleaners, powder and foam carpet cleaners, waxes and polishes such as furniture polishes, floor waxes, shoe creams
  • Textile detergent compositions can be selected from liquid detergents, powder detergents, laundry pretreatments such as bleaches, soaking agents and stain removers, fabric softeners, washing soaps and washing tablets.
  • Food means a raw, cooked, or processed edible substance, ice, beverage or ingredient used or intended for use in whole or in part for human consumption, or chewing gum, gummies, jellies, and confectionaries.
  • a food supplement is a product intended for ingestion that contains a dietary ingredient intended to add further nutritional value to the diet.
  • a dietary ingredient may be one, or any combination, of the following substances: a vitamin, a mineral, an herb or other botanical, an amino acid, a dietary substance for use by people to supplement the diet by increasing the total dietary intake, a concentrate, metabolite, constituent, or extract.
  • Food supplements may be found in many forms such as tablets, capsules, softgels, gelcaps, liquids, or powders.
  • compositions comprise compositions which are intended for use in the diagnosis, cure, mitigation, treatment, or prevention of disease as well as articles (other than food) intended to affect the structure or any function of the body of man or other animals.
  • Crop protection compositions comprise compositions which are intended for the managing of plant diseases, weeds and other pests (both vertebrate and invertebrate) that damage agricultural crops and forestry.
  • compositions according to the invention can further comprise one or more substances, such as, for example: preservatives, abrasives, anti-acne agents, agents to combat skin aging, antibacterial agents, anti-cellulite agents, antidandruff agents, antiinflammatory agents, irritation-preventing agents, irritation-alleviating agents, antimicrobial agents, antioxidants, astringents, sweat-inhibiting agents, antiseptics, antistatics, binders, buffers, carrier materials, chelating agents, cell stimulants, cleaning agents, care agents, hair removal agents, emulsifiers, enzymes, essential oils, fibers, film formers, fixatives, foam formers, foam stabilizers, substances for preventing foaming, foam boosters, fungicides, gelling agents, gel-forming agents, hair care agents, hair shaping agents, hair smoothing agents, moisture-donating agents, moisturizing substances, humectant substances, bleaching agents, strengthening agents, stain removal agents, optical brighteners, impregnating agents, soil repellents
  • compositions according to the invention can also be in microencapsulated form, spray-dried form, in the form of inclusion complexes or in the form of extrusion products.
  • suitable materials with regard to a more targeted release of the scent, for which purpose preferably waxy synthetic substances such as e.g. polyvinyl alcohol are used.
  • the microencapsulation can take place for example by the so-called coacervation method with the help of capsule materials, e.g. made of polyurethane-like substances or soft gelatin.
  • the spray-dried perfume oils can be produced for example by spray-drying an emulsion or dispersion comprising the compounds of formulae (I), (II), (III) or (IV) or a mixture of two or more compounds of the formulae (I), (II), (III) and (IV), or a stereoisomer thereof or a mixture of two or more stereoisomers thereof, as defined above, and composition obtainable by the above method of the invention, wherein carrier substances that can be used are modified starches, proteins, dextrin and vegetable gums.
  • Inclusion complexes can be prepared e.g. by introducing dispersions of fragrance compositions and cyclodextrins or urea derivatives into a suitable solvent, e.g. water.
  • Extrusion products can be produced by melting the compounds of formulae (I), (II), (III) or (IV) or a mixture of two or more compounds of the formulae (I), (II), (III) and (IV), or a stereoisomer thereof or a mixture of two or more stereoisomers thereof, as defined above, or the composition obtainable by the above method of the invention with a suitable wax-like substance and by extrusion with subsequent solidification, optionally in a suitable solvent, e.g. isopropanol.
  • a suitable solvent e.g. isopropanol.
  • the total amount of the compounds of formulae (I), (II), (III) or (IV) or a mixture of two or more compounds of the formulae (I), (II), (III) and (IV), or a stereoisomer thereof or a mixture of two or more stereoisomers thereof, in the compositions according to the present invention is typically adapted to the particular intended use or the intended application and can, thus, vary over a wide range.
  • the customary standard commercial amounts for scents are used.
  • compositions according to the invention can comprise the compounds of formulae (I), (II), (III) or (IV) or a mixture of two or more compounds of the formulae (I), (II), (III) and (IV), or a stereoisomer thereof or a mixture of two or more stereoisomers thereof, as defined above, in an overall amount of from 0.001 to 99.9% by weight, preferably from 0.01 to 90% by weight, more preferably from 0.05 to 80%, in particular from 0.1 to 60% by weight, more particularly from 0.1 to 40% by weight, e.g. from 0.1 to 10% by weight or 0.1 to 15% by weight, based on the total weight of the composition.
  • the compositions comprise the compounds of formulae (I), (II), (III) or (IV) or a mixture of two or more compounds of the formulae (I), (II), (III) and (IV), or a stereoisomer thereof or a mixture of two or more stereoisomers thereof, as defined above, in an overall amount of from 0.001 to 5 weight%, preferably from 0.01 to 2 weight% based on the total weight of the composition.
  • a further aspect of the invention is directed to a method of preparing a composition, in particular an aroma composition, especially a fragranced composition, or for modifying the scent character of a composition, in particular of an aroma composition, especially of a fragranced composition, comprising incorporating a compound of formulae (I), (II), (III) or (IV) or a mixture of two or more compounds of the general formulae (I), (II), (III) and (IV), or of a stereoisomer thereof or of a mixture of two or more stereoisomers thereof as defined above, into said composition.
  • the invention is directed to a method of preparing a composition, in particular an aroma composition, especially a fragranced composition, or for modifying the scent character of a composition, in particular of an aroma composition, especially of a fragranced composition, comprising incorporating a compound of formulae (I), (II) or (III) or a mixture of two or more compounds of the general formulae (I), (II) and (III), or of a stereoisomer thereof or of a mixture of two or more stereoisomers thereof as defined above, into said composition.
  • the invention is directed to a method of preparing a perfume composition, body care composition, hygiene article, cleaning composition, textile detergent composition, food, food supplement, pharmaceutical composition or crop protection composition, comprising incorporating a compound of formulae (I), (II), (III) or (IV) or a mixture of two or more compounds of the general formulae (I), (II), (III) and (IV), or of a stereoisomer thereof or of a mixture of two or more stereoisomers thereof, as defined above, into said perfume composition, body care composition, hygiene article, cleaning composition, textile detergent composition, food, food supplement, pharmaceutical composition or crop protection composition.
  • the invention is directed to a method of preparing a perfume composition, body care composition, hygiene article, cleaning composition, textile detergent composition, food, food supplement, pharmaceutical composition or crop protection composition, comprising incorporating a compound of formulae (I), (II) or (III) or a mixture of two or more compounds of the general formulae (I), (II) and (III), or of a stereoisomer thereof or of a mixture of two or more stereoisomers thereof, as defined above, into said perfume composition, body care composition, hygiene article, cleaning composition, textile detergent composition, food, food supplement, pharmaceutical composition or crop protection composition.
  • 2-(2,4,5-trimethylcyclohex-2-en-1-yl)acetaldehyde is used to impart a green, watery, chrysanthema, grassy, aldehydic, lily of the valley, leathery, terpenic and/or natural note, especially a lily of the valley note, to the above-listed compositions.
  • 6-(1-ethoxyethoxy)-1,4,5-trimethylcyclohex-1-ene is used to impart a watermelon, watery, green, almond, foodlike and technical note to the above-listed compositions.
  • 2,5,6-trimethylcyclohex-2-en-1-ol is used to impart an animalic, indole, technical, solvent, punguent and/or phenolic note to the above-listed compositions.
  • 2,5,6-trimethylcyclohex-2-en-1-ol is used to imparts a phenolic, green banana, nutty, milky and/or warm note to the above-listed compositions.
  • one embodiment of the invention is directed to a method for imparting a green, watery, chrysanthema, grassy, aldehydic, lily of the valley note, leathery, terpenic and/or natural note, especially a lily of the valley note, to a perfume composition, body care composition, hygiene article, cleaning composition, textile detergent composition, food, food supplement, pharmaceutical composition or crop protection composition, which comprises including 2-(2,4,5-trimethylcyclohex-2-en-1-yl)acetaldehyde in a perfume composition, body care composition, hygiene article, cleaning composition, textile detergent composition, food, food supplement, pharmaceutical composition or crop protection composition.
  • Another embodiment of the invention is directed to a method for imparting a watermelon, watery, green, almond, foodlike and technical note to a perfume composition, body care composition, hygiene article, cleaning composition, textile detergent composition, food, food supplement, pharmaceutical composition or crop protection composition, which comprises including 6-(1-ethoxyethoxy)-1,4,5-trimethylcyclohex-1-ene in a perfume composition, body care composition, hygiene article, cleaning composition, textile detergent composition, food, food supplement, pharmaceutical composition or crop protection composition.
  • Another embodiment of the invention is directed to a method for imparting an animalic, indole, technical, solvent, punguent and/or phenolic note to a perfume composition, body care composition, hygiene article, cleaning composition, textile detergent composition, food, food supplement, pharmaceutical composition or crop protection composition, which comprises including 2,5,6-trimethylcyclohex-2-en-1-ol at concentrations of 1000 ppm or more in said perfume composition, body care composition, hygiene article, cleaning composition, textile detergent composition, food, food supplement, pharmaceutical composition or crop protection composition.
  • Another embodiment of the invention is directed to a method for imparting a phenolic, green banana, nutty, milky and/or warm note to a perfume composition, body care composition, hygiene article, cleaning composition, textile detergent composition, food, food supplement, pharmaceutical composition or crop protection composition, which comprises including 2,5,6-trimethylcyclohex-2-en-1-ol at concentrations in the range of from 0.1 to 400 ppm, preferably in the range of from 0.2 to 300 ppm, in particular in the range of from 0.5 to 200 ppm, in said perfume composition, body care composition, hygiene article, cleaning composition, textile detergent composition, food, food supplement, pharmaceutical composition or crop protection composition.
  • a DPX500US (Bruker) 500 MHz NMR spectrometer was used for all NMR measurements. About 20 mg of the material to be investigated was dissolved in about 700 ⁇ L CDCl 3 . 1 HNMR spectra (500 MHz, 700 MHz) and 13 CNMR spectra (125 MHz, 176 MHz) were measured on a C/H - D - 05 Z or a 5 mm CPTI 1H/19F - 13C/15N/D Z-GRD detection probe. Mnova 9.1 was used for evaluation of the spectra. If necessary, 2D-NMR experiments were performed.
  • HPLC-System Agilent Series 1290
  • HPLC-column Ascentis Express RP-Amide, 2.7 ⁇ m, 150*4.6 mm von Supelco® Eluent:
  • reaction mixture was stirred for further 20 h at 0°C. Due to residual starting material further 0.34 g LiAlH 4 (95%, 0.009 mol, 0.03 eq) was added in 6 portions during 30 min. The reaction mixture was stirred for further 20 h at 0°C. 6.4 mL of dist. water was subsequently added in 30 min at a temperature of 0 - 5°C. 6.4 mL of 15% NaOH (aq) was added during 15 min. Further 19.2 mL of dist. water was added and the reaction mixture was stirred for 30 min. 50 g of Na 2 SO 4 was added and the reaction mixture was stirred overnight. The reaction mixture was filtered using a 500 mL G3-suction filter.
  • reaction mixture was stirred for further 20 h at 0°C. 16.4 mL of dist. water was subsequently added in 30 min at a temperature of 5 - 8°C. 16.4 mL of 15% NaOH (aq) were added during 15 min. Further 47.2 mL of dist. water were added and the reaction mixture was stirred for 30 min. 200 g of Na 2 SO 4 was added and the reaction mixture was stirred for 2 h.
  • the reaction mixture was filtered using a G3-suction filter. The filter cake was washed 2 times with 500 mL MTBE. The organic solvent of the filtrate was removed under reduced pressure at 60°C and 750 - 5 mbar.
  • reaction mixture was stirred for further 120 min at 2 - 8°C. 750 mL of dist. water was subsequently added in 5 min at a temperature of 0 - 15°C.
  • the reaction mixture was stirred for further 30 min and after addition of 1.5 L MTBE the phases were separated.
  • the aqueous phase was further extracted using 450 mL MTBE.
  • the organic phases were combined, washed 2 times with 200 mL of sat. sodium chloride solution, dried over Na 2 SO 4 and the solvent was removed under reduced pressure at 40°C, 250 - 5 mbar.
  • a by-product, which can be found in the crude product if the reaction is conducted for more than 5 hours is 6-(2,2-diisobutoxyethyl)-1,3,4-trimethyl-cyclohexene.
  • reaction mixture was stirred for further 30 min and afterwards extracted using 80 mL of methyl-tert-butylether (MTBE).
  • MTBE methyl-tert-butylether
  • the phases were separated and the aqueous phase was extracted with further 25 mL MTBE.
  • the organic phases were combined, washed two times with 10 mL of sat. NaCl solution and dried over Na 2 SO 4 .
  • the solvent was removed under reduced pressure at 40°C, 250 - 5 mbar. 6.3 g of crude product 2-(2,4,5-trimethylcyclohex-2-en-1-yl)ethan-1-ol was obtained as colorless liquid with 90.4 HPLC-a% purity and 89% yield.
  • strips of absorbent paper were dipped into solution containing 0.01 to 10% by weight solutions of the compound (I), (II), (III) or (IV) or mixtures thereof.
  • the solutions were prepared by using triethylcitrate including 250 ppm tocopherol as solvent.
  • 10% by weight stock-solutions of the compound (I), (II), (III) or (IV), or mixtures thereof, in triethylcitrate including 250 ppm tocopherol were prepared, unless otherwise stated.
  • ethanol was typically used as further solvent.
  • the scent impression was olfactively evaluated by a panel of 4 trained perfumer using freshly dipped blotter paper.
  • Fragrance composition 3 corresponds to fragrance composition 1A, where Solution A is replaced by the same amount of Solution C.
  • Fragrance composition 4 corresponds to fragrance composition 1B, where Solution A is replaced by the same amount of Solution D.
  • Fragrance composition 5 corresponds to fragrance composition 2A, where Solution B is replaced by the same amount of Solution E.
  • Fragrance composition 6 corresponds to fragrance composition 2B, where Solution B is replaced by the same amount of Solution F.
  • Deo pump spray 2 corresponds to deo pump spray 1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 2A.
  • Deo pump spray 3 corresponds to deo pump spray 1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 1B.
  • Deo pump spray 4 corresponds to deo pump spray 1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 2B.
  • Deo pump spray 5 corresponds to deo pump spray 1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 3.
  • Deo pump spray 6 corresponds to deo pump spray 1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 4.
  • Deo pump spray 7 corresponds to deo pump spray 1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 5.
  • Deo pump spray 8 corresponds to deo pump spray 1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 6.
  • Table 2 Deo pump spray 2.1 Component INCI amount [wt%] Eumulgin® HRE 60 PEG-60 Hydrogenated Castor Oil 2 Farnesol Deo ingredient 0.2 HYDAGEN® DCMF Chitosan 0.1 glycolic acid (Fa. Merck) glycolic acid 0.04 Fragrance composition 1A Perfume 1.0 Water, deionized ad 100 pH 4
  • Deo pump spray 2.2 corresponds to deo pump spray 2.1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 2A.
  • Deo pump spray 2.3 corresponds to deo pump spray 2.1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 1B.
  • Deo pump spray 2.4 corresponds to deo pump spray 2.1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 2B.
  • Deo pump spray 2.5 corresponds to deo pump spray 2.1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 3.
  • Deo pump spray 2.6 corresponds to deo pump spray 2.1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 4.
  • Deo pump spray 2.7 corresponds to deo pump spray 2.1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 5.
  • Deo pump spray 2.8 corresponds to deo pump spray 2.1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 6.
  • Table 3 Clean Hair Conditioner 1 Component INCI amount [wt.-%] DEHYQUART® L 80 Dicocoylethyl Hydroxyethylmonium Methosulfate (and) Propylene Glycol 1.0 Propylene Glycol solvent 10.0 Eumulgin® HRE 60 PEG-60 Hydrogenated Castor Oil 1.0 LAMESOFT® PO 65 Coco-Glucoside (and) Glyceryl Oleate 1.0 GLUADIN® W 40 Hydrolyzed Wheat Gluten Hydrolyzed Wheat Protein 0.5 Fragrance composition 1A Perfume 1.5 Preservative q.s HYDAGEN® HCMF Chitosan 10.0 (sol.1%) Water, deionized up to 100.0 pH 3.5 - 4.0
  • Clean hair conditioner 2 corresponds to clean hair conditioner 1, where the fragrance compo-sition 1A is replaced by the same amount of the fragrance composition 2A.
  • Clean hair condi-tioner 3 corresponds to clean hair conditioner 1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 1B.
  • Clean hair conditioner 4 corresponds to clean hair conditioner 1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 2B.
  • Clean hair conditioner 5 corresponds to clean hair conditioner 1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 3.
  • Clean hair conditioner 6 corresponds to clean hair conditioner 1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 4.
  • Clean hair conditioner 7 corresponds to clean hair conditioner 1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 5.
  • Clean hair conditioner 8 corresponds to clean hair conditioner 1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 6.
  • Table 4 Face Wash Gel 1 Component INCI amount [wt.-%] PLANTAPON® 611 L Sodium Laureth Sulfate (and) Lauryl Glucoside (and) Cocamidopropyl Betaine 20 PLANTAPON® ACG 35 Disodium Cocoyl Glutamate 1 LAMESOFT® PO 65 Coco-Glucoside (and) Glyceryl Oleate 2 NaCl Sodium Chloride 1.7 PLANTACARE® PS 10 Sodium Laureth Sulfate (and) Lauryl Polyglucose 0.3 Fragrance composition 1A Perfume 1.0 Preservative q.s. Dye q.s. Water Aqua q.s. pH 6-7
  • Face wash gel 2 corresponds to face wash gel 1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 2A.
  • Face wash gel 3 corresponds to face wash gel 1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 1B.
  • Face wash gel 4 corresponds to face wash gel 1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 2B.
  • Face wash gel 5 corresponds to face wash gel 1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 3.
  • Face wash gel 6 corresponds to face wash gel 1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 4.
  • Face wash gel 7 corresponds to face wash gel 1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 5.
  • Face wash gel 8 corresponds to face wash gel 1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 6.
  • Table 5 Foam bath concentrate 1 Component INCI amount [wt%] TEXAPON® K 14 S 70spec. Sodium Myreth Sulfate 25 PLANTACARE® 2000 UP Decyl Glucoside 20 DEHYTON® K Cocamidopropyl Betaine 20 GLUADIN® WP Hydrolyzed Wheat Gluten Hydrolyzed Wheat Protein 1 PLANTACARE® PS 10 Sodium Laureth Sulfate (and) Lauryl Polyglucose 5 Citric Acid, 50 % 0.5 Fragrance composition 1A perfume 2.0 Water, deionized ad 100 pH 5.5
  • Foam bath concentrate 2 corresponds to foam bath concentrate 1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 2A.
  • Foam bath concentrate 3 corresponds to foam bath concentrate 1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 1B.
  • Foam bath concentrate 4 corresponds to foam bath concentrate 1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 2B.
  • Foam bath concentrate 5 corresponds to foam bath concentrate 1, where the fragrance composition 1B is replaced by the same amount of the fragrance composition 3.
  • Foam bath concentrate 6 corresponds to foam bath concentrate 1, where the fragrance composition 1B is replaced by the same amount of the fragrance compo-sition 4.
  • Foam bath concentrate 7 corresponds to foam bath concentrate 1, where the fragrance composition 1B is replaced by the same amount of the fragrance composition 5.
  • Foam bath concentrate 8 corresponds to foam bath concentrate 1, where the fragrance composition 1B is replaced by the same amount of the fragrance composition 6.
  • Hair gel 2 corresponds to hair gel 1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 2A.
  • Hair gel 3 corresponds to hair gel 1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 1B.
  • Hair gel 4 corresponds to hair gel 1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 2B.
  • Hair gel 5 corresponds to hair gel 1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 3.
  • Hair gel 6 corresponds to hair gel 1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 4.
  • Hair gel 7 corresponds to hair gel 1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 5.
  • Hair gel 8 corresponds to hair gel 1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 6.
  • Self-foaming bodywash 2 corresponds to self-foaming bodywash 1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 2A.
  • Self-foaming bodywash 3 corresponds to self-foaming bodywash 1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 1B.
  • Self-foaming bodywash 4 corresponds to self-foaming bodywash 1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 2B.
  • Self-foaming bodywash 5 corresponds to self-foaming bodywash 1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 3.
  • Self-foaming bodywash 6 corresponds to self-foaming bodywash 1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 4.
  • Self-foaming bodywash 7 corresponds to self-foaming bodywash 1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 5.
  • Self-foaming bodywash 8 corresponds to self-foaming bodywash 1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 6.
  • Table 8 Sprayable sun care emulsion 1 Component INCI amount [wt%] EMULGADE® SE-PF Glyceryl Stearate (and) Ceteareth-20 (and) Ceteareth-12 (and) Cetearyl Alcohol (and) Cetyl Palmitate 7.8 EUMULGIN® B 3 Ceteareth-30 4.2 CETIOL® CC Dicaprylyl Carbonate 5.0 CETIOL® OE Dicaprylyl Ether 5.0 Neo Heliopan® BB Benzophenone-3 4.5 Neo Heliopan® AV Ethylhexyl Methoxycinnamate 7.5 Neo Heliopan® 357 Butyl Methoxydibenzoylmethane 2.0 Fragrance composition 1A Perfume 1.5 Eumulgin® HRE 60 PEG-60 Hydrogenated Castor Oil 1.2 Water, de-ionized ad 100 pH 5.5 Viscosity (RVF spindle 2, 20°C, 50 rpm) ⁇ 100 mPas
  • Sprayable sun care emulsion 2 corresponds to sprayable sun care emulsion 1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 2A.
  • Spray-able sun care emulsion 3 corresponds to sprayable sun care emulsion 1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 1B.
  • Sprayable sun care emulsion 4 corresponds to sprayable sun care emulsion 1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 2B.
  • Sprayable sun care emulsion 5 corresponds to sprayable sun care emulsion 1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 3.
  • Sprayable sun care emulsion 6 corresponds to sprayable sun care emulsion 1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 4.
  • Sprayable sun care emulsion 7 corresponds to sprayable sun care emulsion 1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 5.
  • Sprayable sun care emulsion 8 corresponds to sprayable sun care emulsion 1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 6.
  • Sprayable sun protection emulsion 1 Component INCI amount [wt%] EMULGADE® SE-PF Glyceryl Stearate (and) Ceteareth-20 (and) Ceteareth-12 (and) Cetearyl Alcohol (and) Cetyl Palmitate 9.0 Eumulgin B3 Ceteareth-33 6.0 CETIOL® CC Dicaprylyl Carbonate 4.0 Eusolex HMS Homosalate 7.0 Parsol MCX( Ethylhexyl Methoxycinnamate 7.5 Parsol 1789 Butyl Methoxydibenzoylmethane 3.0 Neo Heliopan OS Ethylhexyl Salicylate 5.0 Preservative q.s. Fragrance composition 1A Perfume 1.0 Eumulgin® HRE 60 PEG-60 Hydrogenated Castor Oil 1.2 Water, de-ionized ad 100 pH 6.2
  • Sprayable sun protection emulsion 2 corresponds to sprayable sun protection emulsion 1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 2A.
  • Sprayable sun protection emulsion 3 corresponds to sprayable sun protection emulsion 1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 1B.
  • Sprayable sun protection emulsion 4 corresponds to sprayable sun protection emulsion 1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 2B.
  • Sprayable sun protection emulsion 5 corresponds to sprayable sun protection emulsion 1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 3.
  • Sprayable sun protection emulsion 6 corresponds to sprayable sun protection emulsion 1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 4.
  • Sprayable sun protection emulsion 7 corresponds to sprayable sun protection emulsion 1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 5.
  • Sprayable sun protection emulsion 8 corresponds to sprayable sun protection emulsion 1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 6.
  • Emollient facial gel 1 Component INCI amount [wt%] HISPAGEL® 200 Glycerin (and) Glyceryl Polyacrylate 10 CET-OE-Primasponge®BLUE 0.5 PLANTACARE® PS 10 SodiumLaurethSulfate (and) LaurylPolyglucose 0.6 Fragrance composition 1A 1.0 Water ad 100
  • Emollient facial gel 2 corresponds to emollient facial gel 1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 2A.
  • Emollient facial gel 3 corresponds to emollient facial gel 1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 1B.
  • Emollient facial gel 4 corresponds to emollient facial gel 1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 2B.
  • Emollient facial gel 5 corresponds to emollient facial gel 1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 3.
  • Emollient facial gel 6 corresponds to emollient facial gel 1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 4.
  • Emollient facial gel 7 corresponds to emollient facial gel 1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 5.
  • Emollient facial gel 8 corresponds to emollient facial gel 1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 6.
  • Table 11 2-phases oil foam bath 1 Component INCI amount [wt.-%] PLANTACARE® PS 10 Sodium Laureth Sulfate (and) Lauryl Polyglucose 10 Paraffin oil (low viscosity) 20 TEXAPON® N 70 Sodium Laureth sulfate 13 DEHYTON® PK 45
  • 2-phases oil foam bath 2 corresponds to 2-phases oil foam bath 1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 2A.
  • 2-phases oil foam bath 3 corresponds to 2-phases oil foam bath 1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 1B.
  • 2-phases oil foam bath 4 corresponds to 2-phases oil foam bath 1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 2B.
  • 2-phases oil foam bath 5 corresponds to 2-phases oil foam bath 1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 3.
  • 2-phases oil foam bath 6 corresponds to 2-phases oil foam bath 1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 4.
  • 2-phases oil foam bath 7 corresponds to 2-phases oil foam bath 1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 5.
  • 2-phases oil foam bath 8 corresponds to 2-phases oil foam bath 1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 6.
  • Shampoo 9 corresponds to shampoo 1, where the fragrance composition 1A is re-placed by the same amount of the fragrance composition 2A.
  • Shampoo 10 corresponds to shampoo 2, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 2A.
  • Shampoo 11 corresponds to shampoo 3, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 2A.
  • Shampoo 12 corresponds to shampoo 4, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 2A.
  • Shampoo 13 corresponds to shampoo 5, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 2A.
  • Shampoo 14 corresponds to shampoo 6, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 2A.
  • Shampoo 15 corresponds to shampoo 7, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 2A.
  • Shampoo 16 corresponds to shampoo 8, where the fragrance composition 1A is re-placed by the same amount of the fragrance composition 2A.
  • Shampoo 17 corresponds to shampoo 1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 1B.
  • Shampoo 18 corresponds to shampoo 2, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 1B.
  • Shampoo 19 corresponds to shampoo 3, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 1B.
  • Shampoo 20 corresponds to shampoo 4, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 1B.
  • Shampoo 21 corresponds to shampoo 5, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 1B.
  • Shampoo 22 corresponds to shampoo 6, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 1B.
  • Shampoo 23 corresponds to shampoo 7, where the fragrance composition 1A is re-placed by the same amount of the fragrance composition 1B.
  • Shampoo 24 corresponds to shampoo 8, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 1B.
  • Shampoo 25 corresponds to shampoo 1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 2B.
  • Shampoo 26 corresponds to shampoo 2, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 2B.
  • Shampoo 27 corresponds to shampoo 3, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 2B.
  • Shampoo 28 corresponds to shampoo 4, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 2B.
  • Shampoo 29 corresponds to shampoo 5, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 2B.
  • Shampoo 30 corresponds to shampoo 6, where the fragrance composition 1A is re-placed by the same amount of the fragrance composition 2B.
  • Shampoo 31 corresponds to shampoo 7, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 2B.
  • Shampoo 32 corresponds to shampoo 8, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 2B.
  • Shampoo 33 corresponds to shampoo 1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 3.
  • Shampoo 34 corresponds to shampoo 2, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 3.
  • Shampoo 35 corresponds to shampoo 3, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 3.
  • Shampoo 36 corresponds to shampoo 4, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 3.
  • Shampoo 37 corresponds to shampoo 5, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 3.
  • Shampoo 38 corresponds to shampoo 6, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 3.
  • Shampoo 39 corresponds to shampoo 7, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 3.
  • Shampoo 40 corresponds to shampoo 8, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 3.
  • Shampoo 41 corresponds to shampoo 1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 4.
  • Shampoo 42 corresponds to shampoo 2, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 4.
  • Shampoo 43 corresponds to shampoo 3, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 4.
  • Shampoo 44 corresponds to shampoo 4, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 4.
  • Shampoo 45 corresponds to shampoo 5, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 4.
  • Shampoo 46 corresponds to shampoo 6, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 4.
  • Shampoo 47 corresponds to shampoo 7, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 4.
  • Shampoo 48 corresponds to shampoo 8, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 4.
  • Shampoo 49 corresponds to shampoo 1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 5.
  • Shampoo 50 corresponds to shampoo 2, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 5.
  • Shampoo 51 corresponds to shampoo 3, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 5.
  • Shampoo 52 corresponds to shampoo 4, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 5.
  • Shampoo 53 corresponds to shampoo 5, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 5.
  • Shampoo 54 corresponds to shampoo 6, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 5.
  • Shampoo 55 corresponds to shampoo 7, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 5.
  • Shampoo 56 corresponds to shampoo 8, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 5.
  • Shampoo 57 corresponds to shampoo 1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 6.
  • Shampoo 58 corresponds to shampoo 2, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 6.
  • Shampoo 59 corresponds to shampoo 3, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 6.
  • Shampoo 60 corresponds to shampoo 4, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 6.
  • Shampoo 61 corresponds to shampoo 5, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 6.
  • Shampoo 62 corresponds to shampoo 6, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 6.
  • Shampoo 63 corresponds to shampoo 7, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 6.
  • Shampoo 64 corresponds to shampoo 8, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 6.
  • shower bath 9 corresponds to shower bath 1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 2A.
  • shower bath 10 corresponds to shower bath 2, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 2A.
  • shower bath 11 corresponds to shower bath 3, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 2A.
  • shower bath 12 corresponds to shower bath 4, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 2A.
  • shower bath 13 corresponds to shower bath 5, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 2A.
  • shower bath 14 corresponds to shower bath 6, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 2A.
  • shower bath 15 corresponds to shower bath 7, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 2A.
  • shower bath 16 corresponds to shower bath 8, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 2A.
  • shower bath 17 corresponds to shower bath 1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 1B.
  • shower bath 18 corresponds to shower bath 2, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 1B.
  • shower bath 19 corresponds to shower bath 3, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 1B.
  • shower bath 20 corresponds to shower bath 4, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 1B.
  • shower bath 21 corresponds to shower bath 5, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 1B.
  • shower bath 22 corresponds to shower bath 6, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 1B.
  • shower bath 23 corresponds to shower bath 7, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 1B.
  • shower bath 24 corresponds to shower bath 8, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 1B.
  • shower bath 25 corresponds to shower bath 1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 2B.
  • shower bath 26 corresponds to shower bath 2, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 2B.
  • shower bath 27 corresponds to shower bath 3, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 2B.
  • shower bath 28 corresponds to shower bath 4, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 2B.
  • shower bath 29 corresponds to shower bath 5, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 2B.
  • shower bath 30 corresponds to shower bath 6, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 2B.
  • shower bath 31 corresponds to shower bath 7, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 2B.
  • shower bath 32 corresponds to shower bath 8, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 2B.
  • shower bath 33 corresponds to shower bath 1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 3.
  • shower bath 34 corresponds to shower bath 2, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 3.
  • shower bath 35 corresponds to shower bath 3, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 3.
  • shower bath 36 corresponds to shower bath 4, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 3.
  • shower bath 37 corresponds to shower bath 5, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 3.
  • shower bath 38 corresponds to shower bath 6, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 3.
  • shower bath 39 corresponds to shower bath 7, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 3.
  • shower bath 40 corresponds to shower bath 8, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 3.
  • shower bath 41 corresponds to shower bath 1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 4.
  • shower bath 42 corresponds to shower bath 2, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 4.
  • shower bath 43 corresponds to shower bath 3, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 4.
  • shower bath 44 corresponds to shower bath 4, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 4.
  • shower bath 45 corresponds to shower bath 5, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 4.
  • shower bath 46 corresponds to shower bath 6, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 4.
  • shower bath 47 corresponds to shower bath 7, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 4.
  • shower bath 48 corresponds to shower bath 8, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 4.
  • shower bath 49 corresponds to shower bath 1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 5.
  • shower bath 50 corresponds to shower bath 2, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 5.
  • shower bath 51 corresponds to shower bath 3, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 5.
  • shower bath 52 corresponds to shower bath 4, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 5.
  • shower bath 53 corresponds to shower bath 5, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 5.
  • shower bath 54 corresponds to shower bath 6, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 5.
  • shower bath 55 corresponds to shower bath 7, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 5.
  • shower bath 56 corresponds to shower bath 8, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 5.
  • shower bath 57 corresponds to shower bath 1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 6.
  • shower bath 58 corresponds to shower bath 2, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 6.
  • shower bath 59 corresponds to shower bath 3, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 6.
  • shower bath 60 corresponds to shower bath 4, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 6.
  • shower bath 61 corresponds to shower bath 5, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 6.
  • shower bath 62 corresponds to shower bath 6, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 6.
  • shower bath 63 corresponds to shower bath 7, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 6.
  • shower bath 64 corresponds to shower bath 8, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 6.
  • Table 16 Hydro-alcoholic AP/Deo pump spray 1 Component INCI amount [wt%] Ethanol, cosm. Alcohol 40.0 water, demin.
  • Deo pump spray 2 corresponds to the hydro-alcoholic AP/Deo pump spray 1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 2A.
  • Deo pump spray 3 corresponds to the hydro-alcoholic AP/Deo pump spray 1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 1B.
  • Deo pump spray 4 corresponds to the hydro-alcoholic AP/Deo pump spray 1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 2B.
  • Deo pump spray 5 corresponds to the hydro-alcoholic AP/Deo pump spray 1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 3.
  • Deo pump spray 6 corresponds to the hydro-alcoholic AP/Deo pump spray 1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 4.
  • Deo pump spray 7 corresponds to the hydro-alcoholic AP/Deo pump spray 1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 5.
  • Deo pump spray 8 corresponds to the hydro-alcoholic AP/Deo pump spray 1, where the fragrance composition 1A is re-placed by the same amount of the fragrance composition 6.
  • Table 17 Aerosol 1 Component INCI amount [wt%] ethanol, cosmetic Alcohol 80.0 water, demineralized Aqua 16.7 propylene glycol Propylene Glycol 1.0 Eumulgin® HRE 60 PEG-60 Hydrogenated Castor Oil 1.5 alpha-Bisabolol Bisabolol 0.05 Triclosan Triclosan 0.25 Fragrance composition 1A 1.0
  • Aerosol 2 corresponds to aerosol 1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 2A.
  • Aerosol 3 corresponds to aerosol 1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 1B.
  • Aerosol 4 corresponds to aerosol 1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 2B.
  • Aerosol 5 corresponds to aerosol 1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 3.
  • Aerosol 6 corresponds to aerosol 1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 4.
  • Aerosol 7 corresponds to aerosol 1, where the fragrance composition 1A is re-placed by the same amount of the fragrance composition 5.
  • Aerosol 8 corresponds to aerosol 1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 6.
  • Table 18 Aqueous/alcoholic AP/Deo roll-on 1 Component INCI amount [wt%] ethanol, cosmetic Alcohol 40.0 water, demineralized Aqua 37.0 Hydagen CAT Triethyl Citrate 2.0 Hydagen DCMF Chitosan 10.0 Eumulgin® HRE 60 PEG-60 Hydrogenated Castor Oil 1.5 Chlorhydrol (50% solut.) Aluminium Chlorohydarte 8.0 Klucel M Hydroxypropylcellulose 0.5 Fragrance composition 1A 1.0
  • Table 19 Styling Gel Type "Out of Bed” Phase Component INCI amount [wt.-%] Function I Alcool 96% (Prolabo) Alcohol 96% 12.00 Solvent Luviskol VA 64 (BASF) PVP/VA 4.50 Styling agent Polyox WSR-301 PEG-90M 0.25 Styling agent Methocel E4M Premium EP Hydroxypropyl Methylcellulose 0.60 Thickener DEHYQUART® L 80 Dicocoylethyl Hydroxyethyl-monium Methosulfate (and) Propylene Glycol 0.60 Active agent II. Eumulgin® HRE 60 Hardened castor oil with approx.
  • Emollient III Water, de-ionized Aqua a.d. IV. HISPAGEL® 200 Glycerin (and) Glyceryl Polyacrylate 36.70 Thickener V. Fragrance composition 1A 0.5 pH 6.8, Viscosity (Brookfield RVT 23°C spindle 5, 10 rpm) 220,000 mPas
  • Styling gel according to table 19 where the fragrance composition 1A is replaced by the same amount of the fragrance composition 2A.
  • Styling gel according to table 19 where the fragrance composition 1A is replaced by the same amount of the fragrance composition 1B.
  • Styling gel according to table 19 where the fragrance composition 1A is replaced by the same amount of the fragrance composition 2B.
  • Styling gel according to table 19 where the fragrance composition 1A is replaced by the same amount of the fragrance composition 3.
  • Styling gel according to table 19 where the fragrance composition 1A is replaced by the same amount of the fragrance composition 4.
  • Styling gel according to table 19, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 5.
  • Styling gel according to table 19, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 6.
  • Table 20 Shaving Foam Component INCI amount [wt.-%] Function CUTINA® FS 45 StearicAcid (and) Palmitic Acid 7.6 Surfactant PLANTACARE® 1200 UP Lauryl Glucoside 6.0 Surfactant (inhibitory effect) MONOMULS® 90-O 18 Glyceryl Oleate 1.2 W/O emulsifier EUMULGIN® O20 S Oleth-20 1.2 O/W-emulsifier CETIOL® CC Dicaprylyl Carbonate 2.0 Emollient (low viscosity) DEHYQUART® SP Quaternium-52 0.5 Surfactant TEA (99%) Triethanolamine 4.0 Neutralizer Glycerin Glycerin 3.0 Humectant Propylene Glycol Propylene Glycol 3.0 Humectant Emulgin® HRE 60 Hardened castor oil with approx.
  • Shaving foam according to table 20 where the fragrance composition 1A is replaced by the same amount of the fragrance composition 2A.
  • Shaving foam according to table 20 where the fragrance composition 1A is replaced by the same amount of the fragrance composition 5.
  • Sensitive skin baby shampoo according to table 21, where the fragrance composition 1A is re-placed by the same amount of the fragrance composition 6.
  • Table 25 Body wash for Sensitive Skin Ingredients INCI / Chemistry amount [wt.-%] Function I. Water, demin. Aqua 70.90 TEXAPON® N 70 Sodium Laureth Sulfate 13.00 Surfactant PLANTACARE® 818 UP Coco-Glucoside 3.00 Surfactant LAMESOFT® PO 65 Coco-Glucoside (and) Glyceryl Oleate 5.00 Active, skin conditioning Fragrance composition 1A Fragrance 1.0 Perfume Sodium Benzoate Sodium Benzoate 0.55 Preservative II.
  • Table 26 Gloss Enhancing Shampoo for Sensitive Scalp Ingredients INCI / Chemistry amount [wt.-%] Function I. Water, demin. Aqua 71.60 Luviquat Ultra Care (BASF) Polyquaternium-44 1.50 Active, hair conditioning II. Sodium Benzoate Sodium Benzoate 0.55 Preservative III. TEXAPON® N 70 Sodium Laureth Sulfate 14.30 Surfactant DEHYTON® PK 45 Cocamidopropyl Betaine 5.40 Surfactant MELHYDRANTM LS 4420 Honey Extract 1.00 Active, moisturizing Fragrance composition 1A Fragrance 1.0 Perfume IV. DEHYDOL® LS 2 DEO N Laureth-2 1.00 Thickener V.
  • Triethyl Citrate 5.00 Active, antiperspirant II.
  • Babywipe according to table 28 where the fragrance composition 1A is replaced by the same amount of the fragrance composition 2A. Babywipe according to table 28, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 1B. Babywipe according to table 28, where the fragrance composition 1A is re-placed by the same amount of the fragrance composition 2B. Babywipe according to table 28, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 3. Babywipe according to table 28, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 4. Babywipe according to table 28, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 5. Babywipe according to table 28, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 6.
  • Table 31 Face Day Care Cream Ingredients INCI amount [wt%] Function I Deionized Water Aqua 69.55 Glycerine Glycerin 3.00 Humectant EDETA B Powder Tetrasodium EDTA 0.05 Complexing Agent II Cosmedia® SP Sodium Polyacrylate 0.80 Emulsifying Polymer III Emulgade® PL 68/50 Cetearyl Glucoside (and) 2.00 Self-Emulsifying Base Cetearyl Alcohol Eumulgin® SG Sodium Stearoyl Glutamate 0.50 O/W Emulsifier Monomuls® 90-0-18 Glyceryl Oleate 2.00 W/O Emulsifier Cutina® GMS-V Glyceryl Stearate 2.00 Consistency Giving Factor Cetiol® Sensoft Propylheptyl Caprylate 5.00 Emollient Myritol® 331 Cocoglycerides 3.00 Emollient Cegesoft® PFO Passiflora Incarnata Oil 3.00 Emollient LipodermolTM LS
  • fragrance composition 1A is replaced by the same amount of the fragrance composition 2A.
  • fragrance composition 1A is replaced by the same amount of the fragrance composition 1B.
  • fragrance composition 1A is replaced by the same amount of the fragrance composition 2B.
  • fragrance composition 1A is replaced by the same amount of the fragrance composition 3.
  • fragrance composition 1A is replaced by the same amount of the fragrance composition 4.
  • fragrance composition 1A is replaced by the same amount of the fragrance composition 5.
  • fragrance composition 1A is replaced by the same amount of the fragrance composition 6.
  • Table 32 Face Cleanser Ingredients INCI amount [wt%] Function I Deionized Water Aqua 80.15 EDETA B Powder (BASF) Tetrasodium EDTA 0.05 Complexing Agent Eumulgin® SG Sodium Stearoyl Glutamate 0.30 O/W Emulsifier II Cosmedia® SP Sodium Polyacrylate 1.20 Emulsifier III Isopropylpalmitate Isopropyl palmitate 5.00 Emollient Cetiol® CC Dicaprylyl Carbonate 3.00 Emollient Cetiol® C5 Coco-Caprylate 7.00 Emollient IV Plantacare® 818 UP Coco Glucoside 0.75 Non Ionic Surfactant V Indinyl® CA LS 8998 Water (and) Cassia Angustifolia Seed Polysaccharide 0.50 Smoothing and Moisturizing Active Fragrance composition 1A Fragrance 1.0 Perfume VI Euxyl PE 9010 (Schülke) Phenoxyethanol (and) Ethylhexyl
  • Face cleanser according to table 32 where the fragrance composition 1A is replaced by the same amount of the fragrance composition 2A. Face cleanser according to table 32, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 1B. Face cleanser according to table 32, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 2B. Face cleanser according to table 32, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 3. Face cleanser according to table 32, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 4. Face cleanser according to table 32, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 5. Face cleanser according to table 32, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 6.
  • Sun Care SPF50+, sprayable lotion according to table 33 where the fragrance composition 1A is replaced by the same amount of the fragrance composition 2A.
  • Sun Care SPF50+, sprayable lotion according to table 33 where the fragrance composition 1A is replaced by the same amount of the fragrance composition 1B.
  • Sun Care SPF50+, sprayable lotion according to table 33 where the fragrance composition 1A is replaced by the same amount of the fragrance composition 2B.
  • Table 35 Body lotion Ingredients INCI amount [wt%] Function I Eumulgin® SG Sodium Stearoyl Glutamate 0.40 O/W Emulsifier Cutina® GMS-V Glyceryl Stearate 1.50 Consistency Factor Cetiol® SB 45 Butyrospermum Parkii (Shea) Butter 3.00 Emollient Cetiol® C5 Coco-Caprylate 2.00 Emollient IrwinolTM LS 9890 Octyldodecanol (and) Irvingia Gabonensis (and) Hydrogenated Coco-Glycerides 1.00 Moisturizing Active II Water, demin.
  • Body lotion according to table 35 where the fragrance composition 1A is replaced by the same amount of the fragrance composition 1B.
  • Body lotion according to table 35 where the fragrance composition 1A is replaced by the same amount of the fragrance composition 2A.
  • Body lotion according to table 35 where the fragrance composition 1A is replaced by the same amount of the fragrance composition 2B.
  • Body lotion according to table 35 where the fragrance composition 1A is replaced by the same amount of the fragrance composition 3.
  • Body lotion according to table 35 where the fragrance composition 1A is replaced by the same amount of the fragrance composition 4.
  • Body lotion according to table 35, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 5.
  • Body lotion according to table 35 where the fragrance composition 1A is replaced by the same amount of the fragrance composition 6.
  • Table 36 Shampoo composition Chemical name [CAS No] wt.-% Citric acid [77-92-9] 0.5 Sodium Hydroxide [1310-73-2] 0.7 Amides, coco, N,N-bis(hydroxyethyl) [68603-42-9] 5.5 1-Propanaminium, 3-amino-N-(carboxymethyl)-N,N-dimethyl-, N-(C8-18 and C18-unsaturated acyl) derivatives, inner salts [147170-44-3] 7.0 Fragrance Composition 1A 1.0 Water Add 100
  • Shampoo according to table 36 where the fragrance composition 1A is replaced by the same amount of the fragrance composition 1 B.
  • Shampoo according to table 36 where the fragrance composition 1A is replaced by the same amount of the fragrance composition 2A.
  • Shampoo according to table 36 where the fragrance composition 1A is re-placed by the same amount of the fragrance composition 2B.
  • Shampoo according to table 36 where the fragrance composition 1A is replaced by the same amount of the fragrance composition 3.
  • Shampoo according to table 36 where the fragrance composition 1A is replaced by the same amount of the fragrance composition 4.
  • Shampoo according to table 36 where the fragrance composition 1A is replaced by the same amount of the fragrance composition 5.
  • Shampoo according to table 36 where the fragrance composition 1A is replaced by the same amount of the fragrance composition 6.
  • Table D1 Hand dish cleaner, regular Component INCI amount [wt%] Lutensit ® A-LBN 50 Benzenesulfonic acid, C10-13-alkyl derivatives, sodium salts 25 Lutensol ® GD 70 Alkyl polyglucoside 3 Lutensol ® A 7 N Fatty alcohol ethoxylate 2 Fragrance composition 1A Fragrance 0.7 Dyes Dye 0.05 Water, deionized Aqua ad 100
  • Hand dish cleaner according to table D1 where the fragrance composition 1A is re-placed by the same amount of the fragrance composition 2A.
  • Hand dish cleaner according to table D1 where the fragrance composition 1A is replaced by the same amount of the fragrance composition 1B.
  • Hand dish cleaner according to table D1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 2B.
  • Hand dish cleaner according to table D1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 3.
  • Hand dish cleaner according to table D1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 4.
  • Hand dish cleaner according to table D1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 5.
  • Hand dish cleaner according to table D1, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 6.
  • Table D2 Hand dish cleaner, concentrate: Component INCI amount [wt%] Lutensit ® A-LBN 50 Benzenesulfonic acid, C10-13-alkyl derivatives, sodium salts 40 Lutensit ® AS 2230 Alkylether sulphate 25 Lutensol ® GD 70 Alkyl polyglucoside 7 Lutensol ® A 7 N Fatty alcohol ethoxylate 4 Fragrance composition 1A Perfume 1 Dyes Dye 0.05 Water, de ionized Aqua ad 100
  • Hand dish cleaner according to table D2 where the fragrance composition 1A is re-placed by the same amount of the fragrance composition 2A.
  • Hand dish cleaner according to table D2 where the fragrance composition 1A is replaced by the same amount of the fragrance composition 1B.
  • Hand dish cleaner according to table D2, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 2B.
  • Hand dish cleaner according to table D2 where the fragrance composition 1A is replaced by the same amount of the fragrance composition 3.
  • Hand dish cleaner according to table D2, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 4.
  • Hand dish cleaner according to table D2, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 5.
  • Hand dish cleaner according to table D2, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 6.
  • Table D3 Sanitary cleaner, concentrate Component INCI amount [wt%] Lutensol ® TO 8 isotridecanolethoxylate 5 Phosphoric acid Phosphoric acid 20 Korantin ® PM 2-propyn-1-ol, ethoxylated 3 Citric acid Citric acid 3 Fragrance composition 1A Fragrance 1 Water, deionized Aqua ad 100
  • Table D4 All-purpose cleaner Component INCI amount [wt%] Lutensit ® A-LBA Benzenesulfonic acid, 4-C10-13-sec-alkyl derivatives 1 Ammonia Ammonia 0.2 Lutensol ® CS 6250 Hexan-1-ol, ethoxylated 3 Trilon ® A trisodium nitrilotriacetate 1 Citric acid Citric acid 0.65 Ethanol Ethanol 5 Fragrance composition 1A Perfume 1.5 Water, de ionized Aqua ad 100
  • Anti-bacterial fabric softener according to table D5, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 6.
  • Table D6 Detergent composition 1 Ingredient [CAS No] wt.-% MEA-C10-13 ALKYL BENZENESULFONATE [85480-55-3] 12.4 MEA-COCOATE [66071-80-5] 7.5 C14-15 PARETH-7 [68951-67-7] 5.7 Ethanol [64-17-5] 2 Fragrance Composition 1A 1.0 water balance to 100 g
  • Table D7 Detergent composition 2 Ingredient [wt.-% of solids] n-C 12 H 25 -O-(CH 2 CH 2 O) 3 -SO 3 Na 20.2 n-C 18 H 37 -O(CH 2 CH 2 O) 7 -H 20.2 sodium salt of linear dodecylbenzenesulphonate 20.6 coconut soap, K salt 9 Fragrance Composition 1A 0.8 pH value 8.5 Total solids content (%) 26.7 All amounts in g/100 g of solids content of the respective formulation.
  • Detergent composition according to table D7 where the fragrance composition 1A is replaced by the same amount of the fragrance composition 1B.
  • Detergent composition according to table D7 where the fragrance composition 1A is replaced by the same amount of the fragrance composition 2A.
  • Detergent composition according to table D7 where the fragrance composition 1A is replaced by the same amount of the fragrance composition 2B.
  • Detergent composition according to table D7 where the fragrance composition 1A is replaced by the same amount of the fragrance composition 3.
  • Detergent composition according to table D7 where the fragrance composition 1A is replaced by the same amount of the fragrance composition 4.
  • Detergent composition according to table D7 where the fragrance composition 1A is replaced by the same amount of the fragrance composition 5.
  • Detergent composition according to table D7, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 6.
  • Table D8 Detergent compositions 3A, 3B and 3C Detergent composition 3A 3B 3C Ingredient [in g] n-C 10 -C 13 -alkylbenzene sulfonic acid 10.4 17,9 13 coconut C 12 -C 18 fatty acid 2.5 8.5 8.5 potassium hydroxide 3.4 5 4.4 C 13 C 15 oxo alcohol ethoxylate (7 EO) 5.7 20 7.5 1,2 propyleneglycol 6 8 8 Sodium citrate - dihydrate - 3 3 ethanol 2 2 2 Fragrance Composition 1A 1.0 1.0 1.0 1.0 Additional KOH to pH 9 to pH 8.6 to pH 8.6 water balance to 100 g balance to 100 g balance to 100 g balance to 100 g
  • Detergent composition according to composition 3C of table D8, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 6.
  • Detergent composition according to table D9 where the fragrance composition 1A is replaced by the same amount of the fragrance composition 1B.
  • Detergent composition according to table D9 where the fragrance composition 1A is replaced by the same amount of the fragrance composition 2A.
  • Detergent composition according to table D9 where the fragrance composition 1A is replaced by the same amount of the fragrance composition 2B.
  • Detergent composition according to table D9 where the fragrance composition 1A is replaced by the same amount of the fragrance composition 3.
  • Detergent composition according to table D9 where the fragrance composition 1A is replaced by the same amount of the fragrance composition 4.
  • Detergent composition according to table D9 where the fragrance composition 1A is replaced by the same amount of the fragrance composition 5.
  • Detergent composition according to table D9, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 6.
  • Table D10 Detergent compositions 10A, 10B, 10C and 10D Composition, % by weight Components 10A 10B 10C 10D Linear C 10 C 13 -alkylbenzene sulfonates, sodium salt 6.0 2.0 4.0 4.8 Sodium laureth sulfate + 2 mole ethylene oxide - 4.5 16.0 14.4 Alkyl ether ethoxylate (7 EO): C 12 C 14 -fatty alcohol + 7 mole ethylene oxide 24.0 - - - Alkyl ether ethoxylate (9 EO): C 12 C 14 fatty alcohol + 9 mole ethylene oxide - 17.5 4.0 4.8 Sodium citrate 0.5 0.1 - 0.1 Mono propylene glycol 5.0 1.0 - 1.0 Ethanol 1.5 - - - Toluene sulfonic acid - - - 0.2 Frag
  • Detergent composition according to composition 10A of table D10 where the fragrance composition 1A is replaced by the same amount of the fragrance composition 6.
  • Detergent composition according to composition 10B of table D10 where the fragrance composition 1A is replaced by the same amount of the fragrance composition 1B.
  • Detergent composition according to composition 10B of table D10 where the fragrance composition 1A is replaced by the same amount of the fragrance composition 2A.
  • Detergent composition according to composition 10B of table D10 where the fragrance composition 1A is replaced by the same amount of the fragrance composition 3.
  • Detergent composition according to composition 10B of table D10 where the fragrance composition 1A is replaced by the same amount of the fragrance composition 4.
  • Detergent composition according to composition 10B of table D10 where the fragrance composition 1A is replaced by the same amount of the fragrance composition 5.
  • Detergent composition according to composition 10B of table D10 where the fragrance composition 1A is replaced by the same amount of the fragrance composition 6.
  • Detergent composition according to composition 10C of table D10 where the fragrance composition 1A is replaced by the same amount of the fragrance composition 1B.
  • Detergent composition according to composition 10C of table D10 where the fragrance composition 1A is replaced by the same amount of the fragrance composition 2A.
  • Detergent composition according to composition 10C of table D10 where the fragrance composition 1A is replaced by the same amount of the fragrance composition 3.
  • Table D11 Detergent composition DC1 Ingredients percentage by weight Alkyl Benzene sulfonate 1 7.50% AE3S 2 2.60% AE9 3 0.40% NI 45-7 4 4.40% Citric Acid 3.20% C12-18 Fatty acid 3.10% Amphiphilic polymer 5 0.50% Zwitterionic dispersant 6 1.00% Ethoxylated Polyethyleneimine 7 1.51 % Protease 8 0.89% Enymes 9 0.21% Chelant 10 0.28% Brightener 11 0.09% Solvent 7.35% Sodium Hydroxide 3.70% Fragrance composition 1A 1.0% Water, filler, stucturant to Balance 1 Linear alkylbenenesulfonate having an average aliphatic carbon chain length C11-C12 supplied by Stepan, Northfield Illinois, USA // 2 AE3S is C12-15 alkyl ethoxy (3) sulfate supplied by Stepan, USA // 3 AE9 is C12-14 alcohol ethoxylate, with an average degree of ethoxy
  • the molecular weight of the polyethylene oxide backbone is about 6000 and the weight ratio of the polyethylene oxide to polyvinyl acetate is about 40 to 60 and no more than 1 grafting point per 50 ethylene oxide units.
  • Suitable chelants are, for example, diethylenetetraamine pentaacetic acid (DTPA) supplied by Dow Chemical, Midland, Michigan, USA or Hydroxyethane di phosphonate (HEDP) or diethylene triamine penta(methyl phosphonic) acid supplied by Solutia, St Louis, Missouri, USA; // 11 Fluorescent Brightener 1 is Tinopal® AMS, Fluorescent Brightener 2 supplied by Ciba Specialty Chemicals, Basel, Switzerland
  • Detergent composition according to table D11 where the fragrance composition 1A is replaced by the same amount of the fragrance composition 1B.
  • Detergent composition according to table D11 where the fragrance composition 1A is replaced by the same amount of the fragrance composition 2A.
  • Detergent composition according to table D11 where the fragrance composition 1A is replaced by the same amount of the fragrance composition 2B.
  • Detergent composition according to table D11 where the fragrance composition 1A is replaced by the same amount of the fragrance composition 3.
  • Detergent composition according to table D11 where the fragrance composition 1A is replaced by the same amount of the fragrance composition 4.
  • Detergent composition according to table D11 where the fragrance composition 1A is replaced by the same amount of the fragrance composition 5.
  • Detergent composition according to table D11, where the fragrance composition 1A is replaced by the same amount of the fragrance composition 6.
  • Natalase®, Mannaway® are all products of Novozymes, Bagsvaerd, Denmark.
  • Proteases may be supplied by Genencor International, Palo Alto, California, USA (e.g. Purafect Prime®) or by Novozymes, Bagsvaerd, Denmark (e.g. Liquanase®, Coronase®).
  • Detergent composition according to table D12 where the fragrance composition 1A is replaced by the same amount of the fragrance composition 1B.
  • Detergent composition according to table D12 where the fragrance composition 1A is replaced by the same amount of the fragrance composition 2A.
  • Detergent composition according to table D12 where the fragrance composition 1A is replaced by the same amount of the fragrance composition 2B.
  • Detergent composition according to table D12 where the fragrance composition 1A is replaced by the same amount of the fragrance composition 3.
  • Detergent composition according to table D12 where the fragrance composition 1A is replaced by the same amount of the fragrance composition 4.
  • Detergent composition according to table D12 where the fragrance composition 1A is replaced by the same amount of the fragrance composition 5.
  • Savinase®, Natalase®, Stainzyme®, Lipex®, CellucleanTM, Mannaway® and Whitezyme® are all products of Novozymes, Bagsvaerd, Denmark.
  • Proteases may be supplied by Genencor International, Palo Alto, California, USA (e.g. Purafect Prime®) or by Novozymes, Bagsvaerd, Denmark (e.g. Liquanase®, Coronase®).
  • Detergent composition according to composition 13A of table D13 where the fragrance composition 1A is replaced by the same amount of the fragrance composition 1B.
  • Detergent composition according to composition 13A of table D13 where the fragrance composition 1A is replaced by the same amount of the fragrance composition 2A.
  • Detergent composition according to composition 13A of table D13 where the fragrance composition 1A is replaced by the same amount of the fragrance composition 2B.
  • Detergent composition according to composition 13A of table D13 where the fragrance composition 1A is replaced by the same amount of the fragrance composition 6.
  • Detergent composition according to composition 13B of table D13 where the fragrance composition 1A is replaced by the same amount of the fragrance composition 1 B.
  • Detergent composition according to composition 13B of table D13 where the fragrance composition 1A is replaced by the same amount of the fragrance composition 2A.
  • Detergent composition according to composition 13B of table D13 where the fragrance composition 1A is replaced by the same amount of the fragrance composition 4.

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EP19185187.2A 2019-07-09 2019-07-09 2-(2,4,5-trimethylcyclohex-2-en-1-yl)acetaldehyd und derivate davon und deren verwendung als aromachemikalien Withdrawn EP3763352A1 (de)

Priority Applications (8)

Application Number Priority Date Filing Date Title
EP19185187.2A EP3763352A1 (de) 2019-07-09 2019-07-09 2-(2,4,5-trimethylcyclohex-2-en-1-yl)acetaldehyd und derivate davon und deren verwendung als aromachemikalien
MX2022000408A MX2022000408A (es) 2019-07-09 2020-07-08 2-(2,4,5-trimetilciclohex-2-en-1-il)acetaldehido y derivados y su uso como productos quimicos aromaticos.
CN202080049411.3A CN114080380B (zh) 2019-07-09 2020-07-08 2-(2,4,5-三甲基环己-2-烯-1-基)乙醛和衍生物和它们作为芳香化学品的用途
US17/625,167 US12319647B2 (en) 2019-07-09 2020-07-08 2-(2,4,5-trimethylcyclohex-2-en-1-yl)acetaldehyde and derivatives and their use as aroma chemicals
BR112021024094A BR112021024094A2 (pt) 2019-07-09 2020-07-08 Composto, mistura de compostos, processo para preparar um composto da fórmula geral (i), ou uma mistura de dois ou mais compostos da fórmula geral (i) ou um estereoisômero do mesmo ou uma mistura de dois ou mais estereoisômeros do mesmo, uso de um composto da fórmula (i), (ii), (iii) ou (iv) ou de uma mistura de dois ou mais compostos das fórmulas gerais (i), (ii), (iii) e (iv), ou de um estereoisômero do mesmo ou de uma mistura de dois ou mais estereoisômeros do mesmo, composição, e, método para preparar uma composição de fragrância
PCT/EP2020/069251 WO2021005109A1 (en) 2019-07-09 2020-07-08 2-(2,4,5-trimethylcyclohex-2-en-1-yl)acetaldehyde and derivatives and their use as aroma chemicals
JP2022500654A JP7574272B2 (ja) 2019-07-09 2020-07-08 ２－（２，４，５－トリメチルシクロヘキサ－２－エン－１－イル）アセトアルデヒド及び誘導体、並びにそれらの香料としての使用
EP20740557.2A EP3997057A1 (de) 2019-07-09 2020-07-08 2-(2,4,5-trimethylcyclohex-2-en-1-yl)acetaldehyd und derivate davon und deren verwendung als aromachemikalien

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EP20740557.2A Pending EP3997057A1 (de) 2019-07-09 2020-07-08 2-(2,4,5-trimethylcyclohex-2-en-1-yl)acetaldehyd und derivate davon und deren verwendung als aromachemikalien

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WO (1) WO2021005109A1 (de)

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US20240076258A1 (en) * 2021-02-04 2024-03-07 Maruzen Petrochemical Co., Ltd. Method for producing isobutyl vinyl ether and method for purifying isobutyl vinyl ether
WO2023052289A1 (en) 2021-09-29 2023-04-06 Basf Se Derivatives from 2,5,6-trimethylcyclohex-2-en-1-ol as aroma ingredients
WO2026061972A1 (en) * 2024-09-17 2026-03-26 V. Mane Fils Cyclohexene derivatives having organoleptic properties

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